7-(substituted)-8-(substituted)-9-(substitued amino)-6-demethyl-6-deoxytetracyclines

ABSTRACT

The invention provides compounds of the formulas ##STR1## which are useful as intermediates for the preparation of 6-demethyl-6-deotetracycline antibiotic agents.

This is a divisional of application Ser. No. 08/214,992 filed on Mar.21, 1994, now abandoned which is a continuation of application Ser. No.07/928,598, filed on Aug. 13, 1992, now abandoned.

BACKGROUND OF THE INVENTION

1. Field of the Invention

A The invention relates to novel 4S-(4alpha,12aalpha)!4-(dimethylamino)-7-(substituted)-8-(substituted)-9-(substituted)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamidesherein after called7-(substituted)-8-(substituted)-9-(substituted)-6-demethyl-6-deoxytetracyclines,which are useful as antibiotic agents and exhibit antibacterial activityagainst a wide spectrum of organisms including organisms which areresistant to tetracyclines.

The invention also relates to novel7-(substituted)-8-(substituted)-9-(substituted)-6-demethyl-6-deoxytetracyclineintermediates useful for making the novel compounds of the presentinvention and to novel methods for producing the novel compounds andintermediate compounds.

SUMMARY OF THE INVENTION

This invention is concerned with novel7-(substituted)-8-(substituted)-9-(substituted)-6-demethyl-6-deoxytetracyclines,represented by formulas I and II, which have antibacterial activity;with method of treating infectious diseases in warm blooded animalsemploying these new compound; with methods of treating or controllingveterinary diseases; with pharmaceutical preparations containing thesecompounds; with novel intermediate compounds and processes for theproduction of these compounds. More particularly, this invention isconcerned with compounds of formulas I and II which have enhanced invitro and in vivo antibiotic activity against tetracycline resistantstrains as well as a high level of activity against strains which arenormally susceptible to tetracyclines. ##STR2##

In formula I and II, X is selected from halogen ortrifluoromethanesulfonyloxy; the halogen is selected from bromine,chlorine, fluorine or iodine; R and R¹ are the same or different and areselected from hydrogen; nitro; amino; halogen (selected from chlorine,bromine, fluorine or iodine); cyano; hydroxy; or --NR² R³ ;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl or 1,1-dimethylethyl;

and when R² =methyl or ethyl,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or2-methylpropyl;

and when R² =n-propyl,

R³ =n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or 2-methylpropyl;

and when R² =1-methylethyl,

R³ =n-butyl, 1-methylpropyl or 2-methylpropyl;

and when R² =n-butyl,

R³ =n-butyl, 1-methylpropyl or 2-methylpropyl;

and when R² =1-methylpropyl,

R³ =2-methylpropyl;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ is selected from R⁴ (CH₂)_(n) CO-- or R^(4') (CH₂)_(n) SO₂ --;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=0,

R⁴ is selected from hydrogen; amino; hydroxyamino; straight or branchedmono(C₁ -C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!-oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl(ethyl)amino, ethyl(1-methylethyl)-amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!-hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo-2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; azaheterocyclic groupselected from 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl),4-(1,2,4-triazolyl), 1-tetrazolyl, or 2-tetrazolyl; carboxy(C₂-C₄)alkylamino group selected from aminoacetic acid, α-aminopropionicacid, or α-aminobutyric acid and their optical isomers;(heterocyclo)amino group selected from 2- or 3-furyl, 2- or 3-thienyl,2-, 3- or 4-pyridyl, 2- or 5-pyridazinyl, 2-pyrazinyl, or2-(imidazolyl)amino and their substituted analogues (substitutionselected from straight or branched (C₁ -C₆)alkyl); (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; substituted (C₆-C₁₀)arylamino group selected from 4-(acetamido)phenyl, 2-,3- or4-halophenyl, 2-,3-, or 4-(C₁ -C₄) alkylphenyl, or 2-,3- or4-carboxyphenylamino; (C₇ -C₁₀)arylalkylamino group selected frombenzyl, 2-phenylethyl, α-phenylethyl, (2-naphthyl)methyl,(1-naphthyl)methyl or phenylpropylamino; straight or branched (C₁-C₄)alkyl group selected from methyl, ethyl, n-propyl, 1-methylethyl,n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; (C₃-C₆)cycloalkyl group selected from cyclopropyl, cyclobutyl, cyclopentylor cyclohexyl; substituted (C₃ -C₆)cycloalkyl group (substitutionselected from (C₁ -C₃)alkyl, cyano, amino or (C₁ -C₃)acyl); (C₆-C₁₀)aryl group selected from phenyl, α-naphthyl or β-naphthyl;substituted (C₆ -C₁₀)aryl group (substitution selected from halo, (C₁-C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl; α-hydroxy(C₁ -C₃)alkyl group selected from hydroxymethyl,α-hydroxyethyl,α-hydroxy-1-methylethyl or α-hydroxypropyl; α-mercapto(C₁-C₃)alkyl group selected from mercaptomethyl, α-mercaptoethyl,α-mercapto-1-methyl-ethyl or α-mercaptopropyl; halo(C₁ -C₃)alkyl groupsuch as bromomethyl, fluoromethyl, difluoromethyl, trifluoromethyl,chloromethyl, dichloromethyl, trichloromethyl, 2-fluoroethyl,2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-bromoethyl or 2-iodoethyl; aheterocycle group selected from a five membered aromatic or saturatedring with one N, O, S or Se heteroatom optionally having a benzo orpyrido ring fused thereto: ##STR3##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR4##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR5## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl) such as γ-butyrolactam, γ-butyrolactone, imidazolidinoneor N-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxo-thiomorpholinyl; acyl or haloacyl groupselected from acetyl, propionyl, chloroacetyl, trifluoroacetyl, (C₃ -C₆)cycloalkylcarbonyl such as cyclopropylcarbonyl, cyclobutylcarbonyl,cyclopentylcarbonyl, cyclohexylcarbonyl,(2,3-dimethylcyclopropyl)carbonyl, (1,2-dimethylcyclopropyl)carbonyl,(2-ethylcyclopropyl)carbonyl, (2-methylcyclopentyl)carbonyl or(3-ethylcyclobutyl)carbonyl, (C₆ -C₁₀)aroyl selected from benzoyl ornaphthoyl, halo substituted (C₆ -C₁₀ )aroyl such as pentafluorobenzoyl,4-chlorobenzoyl, 3-bromobenzoyl or 3,4-difluorobenzoyl, (C₁-C₄)alkylbenzoyl such as 4-toluoyl, 2-toluoyl or4-(1-methylethyl)benzoyl, or (heterocycle)carbonyl, the heterocycleselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom optionally having a benzo or pyrido ring fusedthereto: ##STR6##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR7##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR8## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl) such as γ-butyrolactam, γ-butyrolactone, imidazolidinoneor N-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2, 3-dioxo-1-piperazinyl,4-methyl-2, 3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; (C₁ -C₄)alkoxycarbonylgroup selected from methoxycarbonyl, ethoxycarbonyl, straight orbranched propoxylcarbonyl, straight or branched butoxycarbonyl orallyloxycarbonyl; α-aminomethoxycarbonyl; halomethoxycarbonyl; vinyl orsubstituted vinyl group substitution selected from (C₁ -C₃)alkyl group,halogen, (C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl,β-naphthyl, substituted (C₆ -C₁₀)aryl group (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy), halo(C₁ -C₃)alkylgroup such as bromomethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-bromoethyl or2-iodoethyl, a heterocycle group selected from a five membered aromaticor saturated ring with one N, O, S or Se heteroatom optionally having abenzo or pyrido ring fused thereto: ##STR9##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl!; (C₁ -C₄)alkoxygroup such as allyloxy, methoxy, ethoxy, n-propoxy, n-butoxy ortert-butoxy; C₆ -aryloxy group selected from phenoxy or substitutedphenoxy (substitution selected from halo, (C₁ -C₄)alkyl, nitro, cyano,thiol, amino, carboxy, di(C₁ -C₃)alkylamino); (C₇ -C₁₀)aralkyloxy groupsuch as benzyloxy, 1-phenylethyloxy or 2-phenylethyloxy; vinyloxy orsubstituted vinyloxy group (substitution selected from (C₁ -C₄)alkyl,cyano, carboxy, or (C₆ -C₁₀)aryl selected from phenyl, α-naphthyl orβ-naphthyl); R^(a) R^(b) amino(C₁ -C₄)alkoxy group, wherein R^(a) R^(b)is a straight or branched (C₁ -C₄)alkyl selected from methyl, ethyl,n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or1,1-dimethylethyl or R^(a) R^(b) is (CH₂)_(n), n=2-6, or --(CH₂)₂W(CH₂)₂ -- wherein W is selected from --N(C₁ -C₃)alkyl straight orbranched!, --NH, --NOB B is selected from hydrogen or (C₁ -C₃)alkyl!, Oor S; or R^(a) R^(b) aminoxy group, wherein R^(a) R^(b) is a straight orbranched (C₁ -C₄)alkyl selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R^(a) R^(b)is (CH₂)_(n), n=2-6, or --(CH₂)₂ W(CH₂)₂ -- wherein W is selected from--N(C₁ -C₃)-- alkyl straight or branched!, --NH, --NOB B is selectedfrom hydrogen or (C₁ -C₃)alkyl!, O or S; and when R³ =R⁴ (CH₂)_(n) CO--and n=1-4; R⁴ is selected from hydrogen; straight or branched (C₁-C₄)alkyl group selected from methyl, ethyl, n-propyl, 1-methylethyl,n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; (C₃-C₆)cycloalkyl group selected from cyclopropyl, cyclobutyl, cyclopentylor cyclohexyl; substituted (C₃ -C₆)cycloalkyl group (substitutionselected from (C₁ -C₃)alkyl, cyano, amino or (C₁ -C₃)acyl); (C6-C₁₀)aryl group selected from phenyl, α-naphthyl or β-naphthyl;substituted(C₆ -C₁₀)-aryl group (substitution selected from halo, (C₁-C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup such as benzyl, 1-phenylethyl, 2-phenylethyl or phenylpropyl;acyloxy or haloacyloxy group, selected from acetyl, propionyl,chloroacetyl, trichloroacetyl, (C₃ -C₆)cycloalkyl-carbonyl, (C₆-C₁₀)aroyl selected from benzoyl or naphthoyl, halo substituted (C₆-C₁₀)aroyl such as pentafluorobenzoyl, 4-chlorobenzoyl, 3-bromobenzoylor 3,4-difluorobenzoyl, (C₁ -C₄)alkylbenzoyl such as 4-toluoyl,2-toluoyl or 4-(1-methylethyl)benzoyl, (heterocycle)carbonyl, theheterocycle selected from a five membered aromatic or saturated ringwith one N, O, S or Se heteroatom optionally having a benzo or pyridoring fused thereto: ##STR10##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR11##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR12## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; (C₁ -C₄)alkoxy group suchas allyloxy, methoxy, ethoxy, n-propoxy,n-butoxy or tert-butoxy; C₆-aryloxy group selected from phenoxy or substituted phenoxy(substitution selected from halo, (C₁ -C₄)alkyl, nitro, cyano, thiol,amino, carboxy, di(C₁ -C₃)alkylamino); (C₇ -C₁₀)aralkyloxy group such asbenzyloxy, 1-phenylethyloxy or 2-phenylethyloxy; (C₁ -C₃) alkylthiogroup selected from methylthio, ethylthio, propylthio or allylthio; C₆-arylthio group selected from phenylthio or substituted phenylthio(substitution selected from halo, (C₁ -C₄)alkyl, nitro, cyano, thiol,amino, carboxy, di(C₁ -C₃) alkylamino); C₆ -arylsulfonyl group selectedfrom phenylsulfonyl or substituted phenylsulfonyl (substitution selectedfrom halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano,(C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₈)aralkylthio group such as benzylthio, 1-phenylethylthio or2-phenylethylthio; a heterocycle group selected from a five memberedaromatic or saturated ring with one N, O, S or Se heteroatom optionallyhaving a benzo or pyrido ring fused thereto: ##STR13##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR14##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR15## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁ -C₃)alkylthiopyridazinyl, or a six membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom such as2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; hydroxy group; mercaptogroup; α-hydroxy(C₁ -C₃)alkyl group selected from hydroxy-methyl,α-hydroxyethyl or α-hydroxy-1-methylethyl or α-hydroxypropyl; halo(C₁-C₃)alkyl group such as bromomethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-bromoethyl or2-iodoethyl; acyl or haloacyl group selected from acetyl, propionyl,chloroacetyl, trifluoroacetyl, (C₃ -C₆) cycloalkylcarbonyl, (C₆-C₁₀)aroyl selected from benzoyl or naphthoyl, halo substituted (C₆-C₁₀)aroyl such as pentafluorobenzoyl, 4-chlorobenzoyl, 3-bromobenzoyl,3,4-difluorobenzoyl, (C₁ -C₄)alkylbenzoyl such as 4-toluoyl, 2-toluoylor 4-(1-methylethyl)benzoyl, or (heterocycle)carbonyl, the heterocycleselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom optionally having a benzo or pyrido ring fusedthereto: ##STR16##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR17##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR18## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)-aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended o heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; (C₁ -C₄)alkoxycarbonylgroup selected from methoxycarbonyl, ethoxycarbonyl, straight orbranched propoxycarbonyl, allyloxycarbonyl or straight or branchedbutoxycarbonyl; R^(a) R^(b) amino(C₁ -C₄)alkoxy group, wherein R^(a)R^(b) is a straight or branched (C₁ -C₄)alkyl selected from methyl,ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or2-methylpropyl or R^(a) R^(b) is (CH₂)_(n), n=2-6, or --(CH₂)₂ W(CH₂)₂-- wherein W is selected from --N(C₁ -C₃)alkyl straight or branched!,--NH, --NOB B is selected from hydrogen or (C₁ -C₃)alkyl!, O or S; orR^(a) R^(b) aminoxy group, wherein R^(a) R^(b) is a straight or branched(C₁ -C₄)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl,n-butyl, 1-methylpropyl, or 2-methylpropyl or R^(a) R^(b) is (CH₂)_(n) ,n=2-6, or --(CH₂)₂ W(CH₂)₂ -- wherein W is selected from --N(C₁-C₃)alkyl straight or branched!, --NH, --NOB B is selected from hydrogenor (C₁ -C₃)alkyl!, O or S;

and when R³ =R (CH₂)_(n) CO-- and n=2-4,

R⁴ is selected from amino; hydroxyamino; straight or branched mono(C₁-C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!-oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl (ethyl) amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!-hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo-2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; azaheterocyclic groupselected from 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl),4-(1,2,4-triazolyl), 1-tetrazolyl, or 2-tetrazolyl; carboxy(C₂-C₄)alkylamino group selected from aminoacetic acid, α-aminopropionicacid, or α-aminobutyric acid and their optical isomers;(heterocyclo)amino group selected from 2- or 3-furyl, 2- or 3-thienyl,2-, 3- or 4-pyridyl, 2- or 5-pyridazinyl, 2-pyrazinyl, or2-(imidazolyl)amino and their substituted analogues (substitutionselected from straight or branched (C₁ -C₆)alkyl); (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; substituted (C₆-C₁₀)arylamino group selected from 4-(acetamido)phenyl, 2-,3- or4-halophenyl, 2-,3-, or 4-(C₁ -C₄)alkylphenyl, or 2-,3- or4-carboxyphenylamino; (C₇ -C₁₀)arylalkylamino group selected frombenzyl, 2-phenylethyl, α-phenylethyl, (2-naphthyl)methyl,(1-naphthyl)methyl or phenylpropylamino; (C₁ -C₄)alkoxycarbonylaminogroup selected from tert-butoxycarbonylamino, allyloxycarbonylamino,methoxycarbonylamino, ethoxycarbonylamino or propoxycarbonylamino;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=0,

R^(4') is selected from amino; hydroxyamino; straight or branchedmono(C₁ -C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino roupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl (ethyl) amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; azaheterocyclic groupselected from 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl),4-(1,2,4-triazolyl), 1-tetrazolyl, or 2-tetrazolyl; (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; (C₇-C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl orphenylpropylamino; straight or branched (C₁ -C₄)alkyl group selectedfrom methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl or 1,1-dimethylethyl; (C₃ -C₆)cycloalkyl group selectedfrom cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; substituted (C₃-C₆)cycloalkyl group (substitution selected from (C₁ -C₃)alkyl, cyano,amino or (C₁ -C₃)acyl); (C₆ -C₁₀)aryl group selected from phenyl,α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl group (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group such as benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl; halo(C₁ -C₃)alkyl group such as bromomethyl, fluoromethyl,difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl,trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 2-bromoethyl or2-iodoethyl; a heterocycle group selected from a five membered aromaticor saturated ring with one N, O, S or Se heteroatom optionally having abenzo or pyrido ring fused thereto: ##STR19##

    Z=N, O, S or Se

is such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR20##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR21## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; R^(a) R^(b) amino(C₁-C₄)alkoxy group, wherein R^(a) R^(b) is a straight or branched (C₁-C₄)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, or 2-methylpropyl or R^(a) R^(b) is (CH₂)_(n), n=2-6, or--(CH₂)₂ W(CH₂)₂ -- wherein W is selected from --N(C₁ -C₃)alkyl straightor branched!, --NH, --NOB B is selected from hydrogen or (C₁ -C₃)alkyl!,O or S; or R^(a) R^(b) aminoxy group, wherein R^(a) R^(b) is a straightor branched (C₁ -C₄)alkyl selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R^(a) R^(b)is (CH₂)_(n), n=2-6, or --(CH₂)₂ W(CH₂)₂ -- wherein W is selected from--N(C₁ -C₃)alkyl straight or branched!, --NH, --NOB B is selected fromhydrogen or (C₁ -C₃)alkyl!, O or S;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=1-4,

R^(4') is selected from hydrogen; straight or branched (C₁ -C₄)alkylgroup selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; (C₁-C₄)carboxyalkyl group; (C₃ -C₆)cycloalkyl group selected fromcyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; substituted (C₃-C₆)cycloalkyl group (substitution selected from (C₁ -C₃)alkyl, cyano,amino or (C₁ -C₃)acyl); (C₆ -C₁₀)aryl group selected from phenyl,α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl group (substitutionselected from halo, (C₁ -C₄) alkoxy, trihalo(C₁ -C₃) alkyl, nitro,amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy);(C₇ -C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethylor phenylpropyl; (C₁ -C₄)alkoxy group such as allyloxy, methoxy, ethoxy,n-propoxy or tert-butoxy; C₆ -aryloxy group selected from phenoxy orsubstituted phenoxy (substitution selected from halo, (C₁ -C₃)alkyl,nitro, cyano, thiol, amino, carboxy, di(C₁ -C₃)alkylamino); (C₇ -C10)aralkyloxy group such as benzyloxy, 1-phenylethyloxy or2-phenylethyloxy; R^(a) R^(b) amino(C₁ -C₄)alkoxy group, wherein R^(a)R^(b) is a straight or branched (C₁ -C₄)alkyl selected from methyl,ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or2-methylpropyl or R^(a) R^(b) is (CH₂)_(n), n=2-6, or --(CH₂)₂ W(CH₂)₂-- wherein W is selected from --N(C₁ -C₃)-- alkyl straight or branched!,--NH, --NOB B is selected from hydrogen or (C₁ -C₃)alkyl!, O or S; orR^(a) R^(b) aminoxy group, wherein R^(a) R^(b) is a straight or branched(C₁ -C₄)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl,n-butyl, 1-methylpropyl, or 2-methylpropyl or R^(a) R^(b) is (CH₂)_(n),n=2-6, or --(CH₂)₂ W(CH₂)₂ -- wherein W is selected from --N(C₁ -C₃)--alkyl straight or branched!, --NH, --NOB B is selected from hydrogen or(C₁ -C₃)alkyl!, O or S; (C₁ -C₃)alkylthio group selected frommethylthio, ethylthio or n-propylthio; C₆ -arylthio group selected fromphenylthio or substituted phenylthio (substitution selected from halo,(C₁ -C₃)alkyl, nitro, cyano, thiol, amino, carboxy, di(C₁-C₃)alkylamino); (C₇ -C₈)aralkylthio group such as benzylthio,1-phenylethylthio or 2-phenylethylthio; a heterocycle group selectedfrom a five membered aromatic or saturated ring with one N, O, S or Seheteroatom optionally having a benzo or pyrido ring fused thereto:##STR22##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR23##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR24## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; hydroxy group; mercaptogroup; amino; hydroxyamino; straight or branched mono(C₁ -C₆)alkylaminogroup selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₃ -C₈)cycloalkylamino group selected fromcyclopropyl, trans-1,2-dimethylcyclopropyl, cis-1,2-dimethylcyclopropyl,trans-2,3-dimethylcyclopropyl, cis-2,3-dimethylcyclopropyl, cyclobutyl,trans-2,3-dimethylcyclobutyl, cis-2,3-dimethylcyclobutyl, cyclopentyl,cyclohexyl, cycloheptyl, cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo2.2.2!oct-2-ylamino and where appropriate their diastereomers andenantiomers; straight or branched chain di-(C₁ -C₆)alkylamino groupselected from dimethylamino, diethylamino, methyl (ethyl) amino,ethyl(1-methylethyl)amino or a combination of methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₁ -C₆)alkoxyamino group selectedfrom methoxy, ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; azaheterocyclic groupselected from 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl),4-(1,2,4-triazolyl), 1-tetrazolyl, or 2-tetrazolyl; (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; (C₇ -C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl orphenylpropylamino; halo(C₁ -C₃)alkyl group such as bromomethyl,fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl,dichloromethyl, trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl,2,2,2-trifluoroethyl, 2-chloroethyl, 2,2-dichloroethyl,2,2,2-trichloroethyl, 2-bromoethyl or 2-iodoethyl; acyl or haloacylgroup selected from acetyl, propionyl, chloroacetyl, trifluoroacetyl,(C₃ -C₆)cycloalkylcarbonyl, (C₆ -C₁₀)aroyl selected from benzoyl ornaphthoyl, halo substituted (C₆ -C₁₀)aroyl such as pentafluorobenzoyl,4-chlorobenzoyl, 3-bromobenzoyl or 3,4-difluorobenzoyl, (C₁-C₄)alkylbenzoyl such as 4-toluoyl, 2-toluoyl or4-(1-methylethyl)benzoyl, or (heterocycle)carbonyl, the heterocycleselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom optionally having a benzo or pyrido ring fusedthereto: ##STR25##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR26##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR27## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; (C₁ -C₄)alkoxycarbonylgroup selected from methoxycarbonyl, ethoxycarbonyl, straight orbranched propoxycarbonyl, allyloxycarbonyl or straight or branchedbutoxycarbonyl; R⁵ is selected from hydrogen; straight or branched (C₁-C₃)alkyl group selected from methyl, ethyl, n-propyl or 1-methylethyl;(C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl or β-naphthyl; (C₇-C₉)aralkyl group such as benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl; a heterocycle group selected from a five membered aromaticor saturated ring with one N, O, S or Se heteroatom optionally having abenzo or pyrido ring fused thereto: ##STR28##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR29##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR30## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁ -C₃)alkylthiopyridazinyl, or a six membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom such as2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl, 2-dioxothiomorpholinyl; or --(CH₂)_(n) COOR⁷ wheren=0-4 and R⁷ is selected from hydrogen; straight or branched (C₁-C₃)alkyl group selected from methyl, ethyl, n-propyl or 1-methylethyl;or (C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl, β-naphthyl; Ris selected from hydrogen; straight or branched (C₁ -C₃)alkyl groupselected from methyl, ethyl, n-propyl or 1-methylethyl; (C₆ -C₁₀)arylgroup selected from phenyl, α-naphthyl or β-naphthyl; (C₇ -C₉)aralkylgroup such as benzyl, 1-phenylethyl, 2-phenylethyl or phenylpropyl; aheterocycle group selected from a five membered aromatic or saturatedring with one N, O, S or Se heteroatom optionally having a benzo orpyrido ring fused thereto: ##STR31##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR32##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR33## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl, 2-dioxothiomorpholinyl; or --(CH₂)_(n) COOR^(7')where n=0-4 and R^(7') is selected from hydrogen; straight or branched(C₁ -C₃)alkyl selected from methyl, ethyl, n-propyl or 1-methylethyl; or(C₆ -C₁₀)aryl selected from phenyl, α-naphthyl or β-naphthyl; with theproviso that R⁵ and R⁶ cannot both be hydrogen;

or R⁵ and R⁶ taken together are --(CH₂)₂ W(CH₂)₂ --,

wherein W is selected from (CH₂)_(n) and n=0-1, --NH, --N(C₁ -C₃)alkylstraight or branched!, --N(C₁ -C₄)alkoxy, oxygen, sulfur or substitutedcongeners selected from (L or D)proline, ethyl(L or D)prolinate,morpholine, pyrrolidine or piperidine; and the pharmacologicallyacceptable organic and inorganic salts or metal complexes.

Preferred compounds are compounds according to the above formula I andII in which X is selected from halogen or trifluoromethanesulfonyloxy;the halogen is selected from bromine, chlorine, fluorine or iodine; Rand R¹ are the same or different and are selected from hydrogen; nitro;amino; halogen (selected from chlorine, bromine, fluorine or iodine);cyano; hydroxy or --NR² R³ ;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl or 1,1-dimethylethyl;

and when R² =methyl or ethyl, R³ =methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl or 2-methylpropyl;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ is selected from R⁴ (CH₂)_(n) CO-- or R ^(4') (CH₂)_(n) SO₂ --;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=0,

R⁴ is selected from hydrogen; amino; hydroxyamino; straight or branchedmono(C₁ -C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl (ethyl) amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo-2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; azaheterocyclic groupselected from 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl),4-(1,2,4-triazolyl), 1-tetrazolyl, or 2-tetrazolyl; carboxy(C₂-C₄)alkylamino group selected from aminoacetic acid, α-aminopropionicacid, or α-aminobutyric acid and their optical isomers;(heterocyclo)amino group selected from 2- or 3-furyl, 2- or 3-thienyl,2-, 3- or 4-pyridyl, 2- or 5-pyridazinyl, 2-pyrazinyl, or2-(imidazolyl)amino and their substituted analogues (substitutionselected from straight or branched (C₁ -C₆)alkyl); (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; substituted (C₆-C₁₀)arylamino group selected from 4-(acetamido)phenyl, 2-,3- or4-halophenyl, 2-,3-, or 4-(C₁ -C₄)alkylphenyl, or 2-,3- or4-carboxyphenylamino; (C₇ -C₁₀)arylalkylamino group selected frombenzyl, 2-phenylethyl, α-phenylethyl, (2-naphthyl)methyl,(1-naphthyl)methyl or phenylpropylamino; straight or branched (C₁-C₃)alkyl group selected from methyl, ethyl, n-propyl or 1-methylethyl;(C₃ -C₆)cycloalkyl group selected from cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl; substituted (C₃ -C₆)cycloalkyl group(substitution selected from (C₁ -C₃)alkyl, cyano, amino or (C₁-C₃)acyl); (C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl orβ-naphthyl; substituted (C₆ -C₁₀)aryl group (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); α-hydroxy(C₁-C₃)alkyl group selected from hydroxymethyl, α-hydroxyethyl,α-hydroxy-1-methylethyl or α-hydroxypropyl; halo(C₁ -C₃)alkyl group suchas bromomethyl, fluoromethyl, difluoromethyl, trifluoromethyl,chloromethyl, dichloromethyl, trichloromethyl, 2-fluoroethyl,2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-bromoethyl or 2-iodoethyl; aheterocycle group selected from a five membered aromatic or saturatedring with one N, O, S or Se heteroatom optionally having a benzo orpyrido ring fused thereto: ##STR34##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR35##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR36## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁ -C₃)alkylthiopyridazinyl, or a six membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom such as2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; acyl or haloacyl groupselected from acetyl, propionyl, chloroacetyl, trifluoroacetyl, (C₃-C₆)cycloalkylcarbonyl such as cyclopropylcarbonyl, cyclobutylcarbonyl,cyclopentylcarbonyl, cyclohexylcarbonyl,(2,3-dimethylcyclopropyl)carbonyl, (1,2-dimethylcyclopropyl)carbonyl,(2-ethylcyclopropyl)carbonyl, (2-methylcyclopentyl)carbonyl or(3-ethylcyclobutyl)carbonyl, (C₆ -C₁₀)aroyl selected from benzoyl ornaphthoyl, halo substituted (C₆ -C₁₀ )aroyl such as pentafluorobenzoyl,4-chlorobenzoyl, 3-bromobenzoyl or 3,4-difluorobenzoyl, (C₁-C₄)alkylbenzoyl such as 4-toluoyl, 2-methyltoluoyl or4-(1-methylethyl)benzoyl, or (heterocycle)carbonyl, the heterocycleselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom optionally having a benzo or pyrido ring fusedthereto: ##STR37##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR38##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR39## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2, 3-dioxo-1-piperazinyl, 4-methyl-2, 3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; (C₁ -C₄)alkoxycarbonylgroup selected from methoxycarbonyl, ethoxycarbonyl, straight orbranched propoxylcarbonyl, straight or branched butoxycarbonyl orallyloxycarbonyl; α-aminomethoxycarbonyl; halomethoxycarbonyl; vinyl orsubstituted vinyl group substitution selected from (C₁ -C₃)alkyl group,halogen, (C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl,β-naphthyl, substituted (C₆ -C₁₀)aryl group (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy), halo(C₁ -C₃)alkylgroup such as bromomethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-bromoethyl or2-iodoethyl, a heterocycle group selected from a five membered aromaticor saturated ring with one N, O, S or Se heteroatom optionally having abenzo or pyrido ring fused thereto: ##STR40##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, or benzothienyl!; (C₁ -C₄)alkoxy group suchas allyloxy, methoxy, ethoxy, n-propoxy,n-butoxy or tert-butoxy; C₆-aryloxy group selected from phenoxy or substituted phenoxy(substitution selected from halo, (C₁ -C₄)alkyl, nitro, cyano, thiol,amino, carboxy, di(C₁ -C₃)alkylamino); (C₇ -C₁₀)aralkyloxy group such asbenzyloxy, 1-phenylethyloxy or 2-phenylethyloxy; vinyloxy or substitutedvinyloxy group (substitution selected from (C₁ -C₄)alkyl, cyano,carboxy, or (C₆ -C₁₀)aryl selected from phenyl, α-naphthyl orβ-naphthyl);

R^(a) R^(b) amino(C₁ -C₄)alkoxy group, wherein R^(a) R^(b) is a straightor branched (C₁ -C₄)alkyl selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R^(a) R^(b)is (CH₂)_(n), n=2-6, or --(CH₂)₂ W(CH₂)₂ -- wherein W is selected from--N(C₁ -C₃)alkyl straight or branched!, --NH, --NOB B is selected fromhydrogen or (C₁ -C₃)alkyl!, O or S; or R^(a) R^(b) aminoxy group,wherein R^(a) R^(b) is a straight or branched (C₁ -C₄)alkyl selectedfrom methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or2-methylpropyl or R^(a) R^(b) is (CH₂)_(n), n=2-6, or --(CH₂)₂ W(CH₂)₂-- wherein W is selected from --N(C₁ -C₃)alkyl straight or branched!,--NH, --NOB B is selected from hydrogen or (C₁ -C₃)alkyl!, O or S;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=1-4,

R⁴ is selected from hydrogen; (C₁ -C₃)alkyl group is selected frommethyl, ethyl, n-propyl or 1-methylethyl; (C₆ -C₁₀)aryl group selectedfrom phenyl, α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl group(substitution selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl,nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino orcarboxy); acyloxy or haloacyloxy group, selected from acetyl, propionyl,chloroacetyl, trichloroacetyl, (C₃ -C₆) cycloalkylcarbonyl, (C₆-C₁₀)aroyl selected from benzoyl or naphthoyl, halo substituted (C₆-C₁₀)aroyl such as pentafluorobenzoyl, 4-chlorobenzoyl, 3-bromobenzoylor 3,4-difluorobenzoyl, (C₁ -C₄)alkylbenzoyl such as 4-toluoyl,2-toluoyl, 4-(1-methylethyl)benzoyl or (heterocycle)carbonyl, theheterocycle selected from a five membered aromatic or saturated ringwith one N, O, S or Se heteroatom optionally having a benzo or pyridoring fused thereto: ##STR41##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR42##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR43## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl, or a six membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl; (C₁ -C₄)alkoxy group such as allyloxy, methoxy,ethoxy, n-propoxy,n-butoxy or tert-butoxy; R^(a) R^(b) amino(C₁-C₄)alkoxy group, wherein R^(a) R^(b) is a straight or branched (C₁-C₄)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, or 2-methylpropyl or R^(a) R^(b) is (CH₂)_(n), n=2-6, or--(CH₂)₂ W(CH₂)₂ -- wherein W is selected from --N(C₁ -C₃)alkyl straightor branched!, --NH, --NOB B is selected from hydrogen or (C₁ -C₃)alkyl!,O or S; or R^(a) R^(b) aminoxy group, wherein R^(a) R^(b) is a straightor branched (C₁ -C₄)alkyl selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R^(a) R^(b)is (CH₂)_(n), n=2-6, or --(CH₂)₂ W(CH₂)₂ -- wherein W is selected from--N(C₁ -C₃)alkyl straight or branched!, --NH, --NOB B is selected fromhydrogen or (C₁ -C₃)alkyl!, O or S; C₆ -aryloxy group selected fromphenoxy or substituted phenoxy (substitution selected from halo, (C₁-C₄)alkyl, nitro, cyano, thiol, amino, carboxy, di(C₁ -C₃)alkylamino);(C₁ -C₃)alkylthio group selected from methylthio, ethylthio, propylthioor allylthio; C₆ -arylthio group selected from phenylthio or substitutedphenylthio (substitution selected from halo, (C₁ -C₄)alkyl, nitro,cyano, thiol, amino, carboxy, di-(C₁ -C₃)alkylamino); C₆ -arylsulfonylgroup selected from phenylsulfonyl or substituted phenylsulfonyl(substitution selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl,nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino orcarboxy); a heterocycle group selected from a five membered aromatic orsaturated ring with one N, O, S or Se heteroatom optionally having abenzo or pyrido ring fused thereto: ##STR44##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR45##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR46## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl, or a six membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl; hydroxy group; α-hydroxy(C₁ -C₃)alkyl groupselected from hydroxymethyl, α-hydroxyethyl, α-hydroxy-1-methylethyl orα-hydroxypropyl; halo-(C₁ -C₃)alkyl group such as bromomethyl,fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl,dichloromethyl, trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl,2,2,2-trifluoroethyl, 2-bromoethyl or 2-iodoethyl; acyl or haloacylgroup selected from acetyl, propionyl, chloroacetyl, trifluoroacetyl,(C₃ -C₆)cycloalkylcarbonyl, (C₆ -C₁₀ )aroyl selected from benzoyl ornaphthoyl, halo substituted (C₆ -C₁₀)aroyl such as pentafluorobenzoyl,4-chlorobenzoyl, 3-bromobenzoyl or 3,4-difluorobenzoyl, (C₁-C₄)alkylbenzoyl such as 4-toluoyl, 2-toluoyl, or4-(1-methylethyl)-benzoyl, or (heterocycle)carbonyl, the heterocycleselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom optionally having a benzo or pyrido ring fusedthereto: ##STR47##

    Z=N, O S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR48##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR49## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl, or a six membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=2-4,

R⁴ is selected from amino; hydroxyamino; straight or branched mono(C₁-C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl(ethyl)amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group cyclopropoxy, trans-1,2-dimethylcyclopropoxy,cis-1,2-dimethylcyclopropoxy, trans-2,3-dimethylcyclopropoxy,cis-2,3-dimethylcyclopropoxy, cyclobutoxy,trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yl-oxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo- 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2.!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; azaheterocyclic groupselected from 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl),4-(1,2,4-triazolyl), 1-tetrazolyl, or 2-tetrazolyl; carboxy(C₂-C₄)alkylamino group selected from aminoacetic acid, α-aminopropionicacid, or α-aminobutyric acid and their optical isomers; (C₆-C₁₀)arylamino group selected from phenylamino or naphthylamino; (C₇-C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl orphenylpropylamino; (C₁ -C₄)alkoxycarbonylamino group selected fromtert-butoxycarbonylamino, allyloxycarbonylamino, methoxycarbonylamino,ethoxycarbonylamino or propoxycarbonylamino;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=0,

R^(4') is selected from amino; hydroxyamino; straight or branchedmono(C₁ -C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or l-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl(ethyl)amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo-2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; azaheterocyclic groupselected from 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl),4-(1,2,4-triazolyl), 1-tetrazolyl, or 2-tetrazolyl; (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; (C₇-C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl orphenylpropylamino; straight or branched (C₁ -C₃)alkyl group selectedfrom methyl, ethyl, n-propyl or 1-methylethyl; (C₆ -C₁₀)aryl groupselected from phenyl, α-naphthyl or β-naphthyl; substituted (C₆-C₁₀)aryl group (substitution selected from halo, (C₁ -C₄)alkoxy,trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁-C₃)alkylamino or carboxy); a heterocycle group selected from a fivemembered aromatic or saturated ring with one N, O, S or Se heteroatomoptionally having a benzo or pyrido ring fused thereto: ##STR50##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR51##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR52## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or a six membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=1-4,

R^(4') is selected from hydrogen; amino; hydroxyamino; straight orbranched mono(C₁ -C₆)alkylamino group selected from methyl, ethyl,n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl(ethyl)amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethyl-propylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!-hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo-2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; azaheterocyclic groupselected from 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl),4-(1,2,4-triazolyl), 1-tetrazolyl, or 2-tetrazolyl; (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; (C₇-C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl orphenylpropylamino; straight or branched (C₁ -C₃)alkyl group selectedfrom methyl, ethyl, n-propyl or 1-methylethyl; (C₆ -C₁₀)aryl groupselected from phenyl, α-naphthyl or β-naphthyl; substituted (C₆-C₁₀)aryl group (substitution selected from halo, (C₁ -C₄)alkoxy,trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁-C₃)alkylamino or carboxy); (C₁ -C₄)alkoxy group such as allyloxy,methoxy, ethoxy, n-propoxy, n-butoxy, iso-butoxy or tert-butoxy; C₆-aryloxy group selected from phenoxy or substituted phenoxy(substitution selected from halo, (C₁ -C₄)alkyl, nitro cyano, thiol,amino, carboxy, di(C₁ -C₃)alkylamino; (C₇ -C₁₀)aralkyloxy group such asbenzyloxy, 1-phenylethyloxy or 2-phenylethyloxy; (C₁ -C₄)carboxyalkylgroup;

R⁵ is selected from hydrogen; straight or branched (C₁ -C₃)alkyl groupselected from methyl, ethyl, n-propyl or 1-methylethyl; (C₆ -C₁₀)arylgroup selected from phenyl, α-naphthyl or β-naphthyl; (C₇ -C₉)aralkylgroup such as benzyl, 1-phenylethyl, 2-phenylethyl or phenylpropyl; aheterocycle group selected from a five membered aromatic or saturatedring with one N, O, S or Se heteroatom optionally having a benzo orpyrido ring fused thereto: ##STR53##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR54##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR55## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl or pyrimidinyl, or a six memberedsaturated ring with one or two N, O, S or Se heteroatoms and an adjacentappended O heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl,2-dioxothiomorpholinyl; or --(CH₂) COOR⁷ where n=0-4 and R is selectedfrom hydrogen; straight or branched (C₁ -C₃)alkyl group selected frommethyl, ethyl, n-propyl or 1-methylethyl; or (C₆ -C₁₀)aryl groupselected from phenyl, α-naphthyl or β-naphthyl;

R⁶ is selected from hydrogen; straight or branched (C₁ -C₃)alkyl groupselected from methyl, ethyl, n-propyl or 1-methylethyl; (C₆ -C₁₀)arylgroup selected from phenyl, α-naphthyl or β-naphthyl; (C₇ -C₉)aralkylgroup such as benzyl, 1-phenylethyl, 2-phenylethyl or phenylpropyl; aheterocycle group selected from a five membered aromatic or saturatedring with one N, O, S or Se heteroatom optionally having a benzo orpyrido ring fused thereto: ##STR56##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR57##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR58##

(A is selected from hydrogen; straight or branched (C₁ -C₄)alkyl; C₆-aryl; substituted C₆ -aryl (substitution selected from halo, (C₁-C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl, or a six membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl,2-dioxothiomorpholinyl; or (CH₂)_(n) COOR⁷ where n=0-4 and R⁷ isselected from hydrogen; straight or branched (C₁ -C₃)alkyl selected frommethyl, ethyl, n-propyl or 1-methylethyl; or (C₆ -C₁₀)aryl selected fromphenyl, α-naphthyl or β-naphthyl; with the proviso that R⁵ and R⁶ cannotboth be hydrogen;

or R⁵ and R⁶ taken together are --(CH₂)₂ W(CH₂)₂ --, wherein W isselected from (CH₂)_(n) and n=0-1, --NH, --N(C₁ -C₃)alkyl straight orbranched!, --N(C₁ -C₄)alkoxy, oxygen, sulfur or substituted congenersselected from (L or D)proline, ethyl(L or D)prolinate, morpholine,pyrrolidine or piperidine; and the pharmacologically acceptable organicand inorganic salts or metal complexes.

Particularly preferred compounds are compounds according to the aboveformula I and II in which X is selected from halogen ortrifluoromethanesulfonyloxy; the halogen is selected from bromine,chlorine, fluorine or iodine;

R and R¹ are the same or different and are selected from hydrogen;nitro; amino; halogen (selected from chlorine, bromine, fluorine oriodine); cyano; hydroxy; or --NR² R³ ;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl or 1,1-dimethylethyl;

and when R² =methyl or ethyl,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or2-methylpropyl;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ is selected from R⁴ (CH₂)_(n) CO-- or R⁴ (CH₂)_(n) SO₂ --;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=0,

R⁴ is selected from hydrogen; amino; hydroxyamino; straight or branchedmono(C₁ -C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!-oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆) alkylamino group selected from dimethylamino,diethylamino, methyl (ethyl)amino, ethyl (1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl orl-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)-alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo-2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo- 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; azaheterocyclic groupselected from 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl),4-(1,2,4-triazolyl), 1-tetrazolyl, or 2-tetrazolyl; (heterocyclo)aminogroup selected from 2- or 3-furyl, 2- or 3-thienyl, 2-, 3- or 4-pyridyl,2- or 5-pyridazinyl, 2-pyrazinyl, or 2-(imidazolyl)amino and theirsubstituted analogues (substitution selected from straight or branched(C₁ -C₆)alkyl); (C₆ -C₁₀)arylamino group selected from phenylamino ornaphthylamino; substituted (C₆ -C₁₀)arylamino group selected from4-(acetamido)phenyl, 2-,3- or 4-halophenyl, 2-,3-, or 4-(C₁-C₄)alkylphenyl, or 2-,3- or 4-carboxyphenylamino; (C₇-C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl orphenylpropylamino; straight or branched (C₁ -C₃)alkyl group selectedfrom methyl, ethyl, n-propyl or 1-methylethyl; (C₃ -C₆)cycloalkyl groupselected from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;substituted (C₃ -C₆)cycloalkyl group (substitution selected from (C₁-C₃)alkyl, cyano, amino or (C₁ -C₃)acyl); (C₆ -C₁₀)aryl group selectedfrom phenyl, α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl group(substitution selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl,nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃) alkylamino orcarboxy); α-hydroxy(C₁ -C₃)alkyl group selected from hydroxymethyl,α-hydroxyethyl, α-hydroxy-1-methylethyl or α-hydroxypropyl; halo(C₁-C₃)alkyl group such as bromomethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-bromoethyl or2-iodoethyl; a heterocycle group selected from a five membered aromaticor saturated ring with one N, O, S or Se heteroatom optionally having abenzo or pyrido ring fused thereto: ##STR59##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR60##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR61##

(A is selected from hydrogen; straight or branched (C₁ -C₄)alkyl; C₆-aryl; substituted C₆ -aryl (substitution selected from halo, (C₁-C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl, or a six membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl; acyl or haloacyl group selected from acetyl,propionyl, chloroacetyl, trifluoroacetyl, (C₃ -C₆)cycloalkylcarbonylsuch as cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl,cyclohexylcarbonyl, (2,3-dimethylcyclopropyl)carbonyl,(1,2-dimethylcyclopropyl)carbonyl, (2-ethylcyclopropyl)carbonyl,(2-methylcyclopentyl)carbonyl or (3-ethylcyclobutyl)carbonyl, (C₆ -C₁₀)aroyl selected from benzoyl or naphthoyl, halo substituted (C₆-C₁₀)aroyl such as pentafluorobenzoyl, 4-chlorobenzoyl, 3-bromobenzoylor 3,4-difluorobenzoyl, (C₁ -C₄)alkylbenzoyl such as 4-toluoyl,2-methylbenzoyl or 4-(1-methylethyl)benzoyl, or (heterocycle)carbonyl,the heterocycle selected from a five membered aromatic or saturated ringwith one N, O, S or Se heteroatom optionally having a benzo or pyridoring fused thereto: ##STR62##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR63##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR64## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)alkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl, or a six membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl; (C₁ -C₄)alkoxycarbonyl group selected frommethoxycarbonyl, ethoxycarbonyl, straight or branched propoxylcarbonyl,straight or branched butoxycarbonyl or allyloxycarbonyl;α-aminomethoxycarbonyl; halomethoxycarbonyl; vinyl or substituted vinylgroup substitution selected from (C₁ -C₃)alkyl group, halogen, (C₆-C₁₀)aryl group selected from phenyl, α-naphthyl, β-naphthyl,substituted (C₆ -C₁₀)aryl group (substitution selected from halo, (C₁-C₄)alkoxy, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃) alkylamino or carboxy),halo(C₁ -C₃)alkyl group such as bromomethyl, fluoromethyl,difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl,trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-bromoethyl or 2-iodoethyl, a heterocycle group selected from a fivemembered aromatic or saturated ring with one N, O, S or Se heteroatomoptionally having a benzo or pyrido ring fused thereto: ##STR65##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, or benzothienyl!; (C₁ -C₄)alkoxy group suchas allyloxy, methoxy, ethoxy, n-propoxy, n-butoxy or tert-butoxy; C₆-aryloxy group selected from phenoxy or substituted phenoxy(substitution selected from halo, (C₁ -C₄)alkyl); (C₇ -C₁₀)aralkyloxygroup such as benzyloxy, 1-phenylethyloxy or 2-phenylethyloxy;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=1-4,

R⁴ is selected from hydrogen; (C₁ -C₃)alkyl group selected from methyl,ethyl, n-propyl or 1-methylethyl; (C ₆ -C₁₀)aryl group selected fromphenyl, α-naphthyl or β-naphthyl; substituted (C ₆ -C₁₀)aryl group(substitution selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl,nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino orcarboxy); acyloxy or haloacyloxy group, selected from acetyl, propionyl,chloroacetyl, trichloroacetyl, (C₃ -C₆) cycloalkylcarbonyl, (C₆-C₁₀)aroyl selected from benzoyl or naphthoyl, halo substituted (C₆-C₁₀)aroyl such as pentafluorobenzoyl, 4-chlorobenzoyl, 3-bromobenzoylor 3,4-difluorobenzoyl, (C₁ -C₄)alkylbenzoyl such as 4-toluoyl,2-toluoyl, 4-(1-methylethyl) benzoyl or (heterocycle)carbonyl, theheterocycle selected from a five membered aromatic or saturated ringwith one N, O, S or Se heteroatom optionaly having a benzo or pyridoring fused thereto: ##STR66##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR67##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR68## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)alkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl or pyrazinyl, or a sixmembered saturated ring with one or two N, O, S or Se heteroatoms and anadjacent appended O heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl; (C₁ -C₄)alkoxy group such as allyloxy, methoxy,ethoxy, n-propoxy, n-butoxy or tert-butoxy; C₆ -aryloxy group selectedfrom phenoxy or substituted phenoxy (substitution selected from halo,(C₁ -C₄)alkyl, nitro, cyano, thiol, amino, carboxy, di-(C₁-C₃)alkylamino); (C₁ -C₃)alkylthio group selected from methylthio,ethylthio, propylthio or allylthio; C₆ -arylthio group selected fromphenylthio or substituted phenylthio (substitution selected from halo,(C₁ -C₄)alkyl, nitro, cyano, thiol, amino, carboxy, di-(C₁-C₃)alkylamino); C₆ -arylsulfonyl group selected from phenylsulfonyl orsubstituted phenylsulfonyl (substitution selected from halo, (C₁-C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); a heterocycle groupselected from a five membered aromatic or saturated ring one N, O, S orSe heteroatom optionally having a benzo or pyrido ring fused thereto:##STR69##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR70##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR71## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl or pyrazinyl, or a sixmembered saturated ring with one or two N, O, S or Se heteroatoms and anadjacent appended O heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2 , 3-dioxo-1-piperazinyl, 4-methyl-2 , 3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl; hydroxy group; α-hydroxy(C₁ -C₃)alkyl groupselected from hydroxymethyl, α-hydroxyethyl, α-hydroxy-1-methylethyl orα-hydroxypropyl; halo(C₁ -C₃)alkyl group such as bromomethyl,fluoromethyl, difluoromethyl, trifluoroethyl, chloromethyl,dichloromethyl, trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl,2,2,2-trifluoromethyl, 2-bromoethyl or 2-iodoethyl; acyl or haloacylgroup selected from acetyl, propionyl, chloroacetyl, trifluoroacetyl,(C₃ -C₆)cycloalkylcarbonyl, (C₆ -C₁₀)aroyl selected from benzoyl ornaphthoyl, halo substituted (C₆ -C₁₀)aroyl such as pentafluorobenzoyl,4-chlorobenzoyl, 3-bromophenylcarbonyl or 3,4-difluorobenzoyl, (C₁-C₄)alkylbenzoyl such as from 4-toluoyl, 2-toluoyl or4-(1-methylethyl)benzoyl, or (heterocycle)carbonyl, the heterocycleselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom optionally having a benzo or pyrido ring fusedthereto: ##STR72##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR73##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR74## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl or pyrazinyl, or a sixmembered saturated ring with one or two N, O, S or Se heteroatoms and anadjacent appended O heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=2-4,

R⁴ is selected from amino; hydroxyamino; straight or branched mono(C₁-C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!-oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl(ethyl)amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl orl-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo-2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; azaheterocyclic groupselected from 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl),4-(1,2,4-triazolyl), 1-tetrazolyl, or 2-tetrazolyl; (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; (C₇-C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl orphenylpropylamino; (C₁ -C₄)alkoxycarbonylamino group selected fromtert-butoxycarbonylamino, allyloxycarbonylamino, methoxycarbonylamino,ethoxycarbonylamino or propoxycarbonylamino;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=0,

R^(4') is selected from amino; hydroxyamino; straight or branchedmono(C₁ -C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl(ethyl)amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo-2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; azaheterocyclic groupselected from 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl),4-(1,2,4-triazolyl), 1-tetrazolyl, or 2-tetrazolyl; (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; (C₇-C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl orphenylpropylamino; straight or branched (C₁ -C₃)alkyl group selectedfrom methyl, ethyl, n-propyl or 1-methylethyl; (C₆ -C₁₀)aryl groupselected from phenyl, α-naphthyl or β-naphthyl; substituted (C₆-C₁₀)aryl group (substitution selected from halo, (C₁ -C₄)alkoxy,trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁-C₃)alkylamino or carboxy); a heterocycle group selected from a fivemembered aromatic or saturated ring with one N, O, S or Se heteroatomoptionally having a benzo or pyrido ring fused thereto: ##STR75##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=1-4,

R^(4') is selected from hydrogen; amino; hydroxyamino; straight orbranched mono(C₁ -C₆)alkylamino group selected from methyl, ethyl,n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl (ethyl) amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo-2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; azaheterocyclic groupselected from 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl),4-(1,2,4-triazolyl), 1-tetrazolyl, or 2-tetrazolyl; (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; (C₇-C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl orphenylpropylamino; straight or branched (C₁ -C₃)alkyl group selectedfrom methyl, ethyl, n-propyl or 1-methylethyl;

R⁵ is selected from hydrogen; straight or branched (C₁ -C₃)alkyl groupselected from methyl, ethyl, n-propyl or 1-methylethyl; (C₆ -C₁₀)arylgroup selected from phenyl, α-naphthyl or β-naphthyl; (C₇ -C₉)aralkylgroup such as benzyl, 1-phenylethyl, 2-phenylethyl or phenylpropyl; or--(CH₂)_(n) COOR⁷ where n=0-4 and R⁷ is selected from hydrogen; straightor branched (C₁ -C₃)alkyl group selected from methyl, ethyl, n-propyl or1-methylethyl; or (C₆ -C₁₀)aryl group selected from phenyl, α-naphthylor β-naphthyl;

R⁶ is selected from hydrogen; straight or branched (C₁ -C₃)alkyl groupselected from methyl, ethyl, n-propyl or 1-methylethyl; (C₆ -C₁₀)arylgroup selected from phenyl, α-naphthyl or β-naphthyl; (C₇ -C₉)aralkylgroup such as benzyl, 1-phenylethyl, 2-phenylethyl or phenylpropyl; or(CH₂)_(n) COOR^(7') where n=0-4 and R^(7') is selected from hydrogen;straight or branched (C₁ -C₃)alkyl selected from methyl, ethyl, n-propylor 1-methylethyl; or (C₆ -C₁₀)aryl selected from phenyl, α-naphthyl orβ-naphthyl; with the proviso that R⁵ and R⁶ cannot both be hydrogen;

or R⁵ and R⁶ taken together are --(CH₂)₂ W(CH₂)₂ --, wherein W isselected from (CH₂)_(n) and n=0-1, --NH, --N(C₁ -C₃)alkyl straight orbranched!, --N(C₁ -C₄)alkoxy, oxygen, sulfur or substituted congenersselected from (L or D)proline, ethyl(L or D)prolinate, morpholine,pyrrolidine or piperidine; and the pharmacologically acceptable organicand inorganic salts or metal complexes.

Most particularly preferred compounds are compounds according to theabove formula I and II in which X is selected from halogen ortrifluoromethanesulfonyloxy; the halogen is selected from bromine,chlorine, fluorine or iodine;

R and R¹ are the same or different and are selected from hydrogen;nitro; amino; halogen (selected from chlorine, bromine, fluorine oriodine); cyano; hydroxy; or --NR R³ ;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl or 1,1-dimethylethyl;

and when R² =methyl or ethyl,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or2-methylpropyl;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ selected from R⁴ (CH₂).sub. CO-- or R^(4') (CH₂)_(n) SO₂ --;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=0,

R⁴ is selected from hydrogen; amino; hydroxyamino; straight or branchedmono(C₁ -C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!-oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl (ethyl) amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.l!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)arylalkylaminogroup selected from benzyl, 2-phenylethyl, α-phenylethyl,(2-naphthyl)methyl, (1-naphthyl)methyl or phenylpropylamino; straight orbranched (C₁ -C₂)alkyl group selected from methyl or ethyl; (C₆-C₁₀)aryl group selected from phenyl, α-naphthyl or β-naphthyl;substituted (C₆ -C₁₀)aryl group (substitution selected from halo, (C₁-C₄)alkoxy, nitro, amino); α-hydroxy(C₁ -C₃)alkyl group selected fromhydroxymethyl; halo(C₁ -C₃)alkyl group such as bromomethyl,fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl,dichloromethyl, trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl,2,2,2-trifluoroethyl, 2-bromoethyl or 2-iodoethyl; a heterocycle groupselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom optionally having a benzo or pyrido ring fusedthereto: ##STR76##

    Z=N, O, S or Se

such as indolyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 2-pyrrolinyl,tetrahydrofuranyl, furanyl, benzofuranyl, tetrahydrothienyl or thienyl,or a five membered aromatic ring with two N, O, S or Se heteroatomsoptionally having a benzo or pyrido ring fused thereto: ##STR77##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, indazolyl, thiazolyl orbenzothiazolyl; (C₁ -C₄)alkoxycarbonyl group selected frommethoxycarbonyl, ethoxycarbonyl, straight or branched propoxycarbonyl,straight or branched butoxycarbonyl or allyloxycarbonyl;α-aminomethoxycarbonyl; halomethoxycarbonyl; vinyl or substituted vinylgroup substitution selected from (C₁ -C₃)alkyl group, (C₆ -C₁₀)arylgroup selected from phenyl, α-naphthyl, β-naphthyl!; (C₁ -C₄)alkoxygroup such as allyloxy, methoxy, ethoxy, n-propoxy, n-butoxy ortert-butoxy; C₆ -aryloxy group selected from phenoxy or substitutedphenoxy (substitution selected from halo, (C₁ -C₄)alkyl); (C₇-C₁₀)aralkyloxy group such as benzyloxy, 1-phenylethyloxy or2-phenylethyloxy;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=1-4,

R⁴ is selected from hydrogen; (C₁ -C₂)alkyl group selected from methylor ethyl; (C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl orβ-naphthyl; substituted(C₆ -C₁₀)aryl group (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl); acyloxy or haloacyloxygroup, selected from acetyl, propionyl, chloroacetyl, trichloroacetyl,(C₃ -C₆)cycloalkylcarbonyl, (C₆ -C₁₀)aroyl selected from benzoyl ornaphthoyl, halo substituted (C₆ -C₁₀)aroyl such as pentafluorobenzoyl,4-chlorobenzoyl, 3-bromobenzoyl or 3,4-difluorobenzoyl, (C₁-C₄)alkylbenzoyl such as 4-toluoyl, 2-toluoyl, 4-(1-methylethyl)benzoylor (heterocycle)carbonyl, the heterocycle selected from a five memberedaromatic or saturated ring with one N heteroatom optionally having abenzo or pyrido ring fused thereto: ##STR78##

    Z=N, O, S or Se

such as tetrahydrofuranyl, furanyl, benzofuranyl, tetrahydrothienyl,thienyl or benzothienyl, or a five membered aromatic ring with two N, O,S or Se heteroatoms optionally having a benzo or pyrido ring fusedthereto: ##STR79##

    Z or Z.sup.1 =N, O, S or Se

such as pyrazolyl, benzimidazolyl, benzoxazolyl, indazolyl, thiazolyl orbenzothiazolyl, or a six membered aromatic ring with one or two Nheteroatoms such as pyridyl or pyridazinyl; (C₁ -C₄)alkoxy group such asallyloxy, methoxy, ethoxy, n-propoxy, n-butoxy or tert-butoxy;α-hydroxy(C₁ -C₃)alkyl group selected from hydroxymethyl,α-hydroxyethyl, α-hydroxy-1-methylethyl or α-hydroxypropyl; halo(C₁-C₃)alkyl group such as bromomethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-bromoethyl or2-iodoethyl;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=2-4,

R⁴ is selected from amino; hydroxyamino; straight or branched mono(C₁-C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈) cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl (ethyl) amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.l!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)arylalkylaminogroup selected from benzyl, 2-phenylethyl, α-phenylethyl,(2-naphthyl)methyl, (1-naphthyl)methyl or phenylpropylamino; (C₁-C₄)alkoxycarbonylamino group selected from tert-butoxycarbonylamino,allyloxycarbonylamino, methoxycarbonylamino, ethoxycarbonylamino orpropoxycarbonylamino;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=0,

R⁴ is selected from amino; hydroxyamino; straight or branched mono(C₁-C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or l-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈) cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.l!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl(ethyl)amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl orl-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,.cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers;

(C₇ -C₁₀)aralkoxyamino group selected from benzyloxy, 2-phenylethoxy,α-phenylethoxy, (2-naphthyl)methoxy, (1-naphthyl)methoxy, orphenylpropoxyamino; (C₂ -C₈)azacycloalkyl group selected fromaziridinyl, azetidinyl, pyrrolidinyl, pyrrolinyl, piperidinyl,2-methylpyrrolidinyl, cis-3,4-dimethylpyrrolidinyl,trans-3,4-dimethylpyrrolidinyl, 2-azabicyclo 2.1.1!hex-2-yl,5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo- 2.2.1!hept-2-yl, 7-azabicyclo2.2.1!hept-7-yl, or 2-azabicyclo 2.2.2!oct-2-yl and where appropriatetheir diastereomers and enantiomers; azaheterocycloalkyl group selectedfrom morpholinyl, piperazinyl, 4-methylpiperazinyl,4-hydroxypiperazinyl, 4-(C₁ -C₄)-alkoxypiperazinyl, thiamorpholinyl,tetrahydro-1,2-oxazinyl, isoxazolidinyl, pyrazolidinyl,2-methylpyrazolidinyl, 2,5-diazabicyclo 2.2.2!hept-2-yl, or2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and where appropriate theirdiastereomers and enantiomers; (C₇ -C₁₀)arylalkylamino group selectedfrom benzyl, 2-phenylethyl, α-phenylethyl, (2-naphthyl)methyl,(1-naphthyl)methyl or phenylpropylamino; straight or branched (C₁-C₂)alkyl group selected from methyl or ethyl; (C₆ -C₁₀)aryl groupselected from phenyl, α-naphthyl or β-naphthyl;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=1-4,

R^(4') is selected from hydrogen; straight or branched (C₁ -C₂)alkylgroup selected from methyl or ethyl; R⁵ is selected from hydrogen;straight or branched (C₁ -C₃)alkyl group selected from methyl, ethyl,n-propyl or 1-methylethyl; (C₆ -C₁₀)aryl group selected from phenyl,α-naphthyl or β-naphthyl; (C₇ -C₉)aralkyl group such as benzyl; or--(CH₂)_(n) COOR⁷ where n=0-4 and

R⁷ is selected from hydrogen; straight or branched (C₁ -C₃)alkyl groupselected from methyl, ethyl, n-propyl or 1-methylethyl; or (C₆ -C₁₀)arylgroup selected from phenyl, α-naphthyl, β-naphthyl;

R⁶ is selected from hydrogen; straight or branched (C₁ -C₃)alkyl groupselected from methyl, ethyl, n-propyl or 1-methylethyl; (C₆ -C₁₀)arylgroup selected from phenyl, α-naphthyl or β-naphthyl; (C₇ -C₉)aralkylgroup such as benzyl; or --(CH₂)_(n) COOR⁷ where n=0-4 and

R⁷ is selected from hydrogen; straight or branched (C₁ -C₃)alkyl groupselected from methyl, ethyl, n-propyl or 1-methylethyl; or (C₆ -C₁₀)arylgroup selected from phenyl, α-naphthyl, β-naphthyl; with the provisothat R⁵ and R⁶ cannot both be hydrogen;

or R⁵ and R⁶ taken together are --(CH₂)₂ W(CH₂)₂ --, wherein W isselected from (CH₂)_(n) and n=0-1, --NH, --N(C₁ -C₃)alkyl straight orbranched!, --N(C₁ -C₄)alkoxy, oxygen, sulfur or substituted congenersselected from (L or D)proline, ethyl(L or D)prolinate, morpholine,pyrrolidine or piperidine; and the pharmacologically acceptable organicand inorganic salts or metal complexes.

Compounds of special interest are compounds according to the aboveformula I and II in which X is selected from halogen ortrifluoromethanesulfonyloxy; the halogen is selected from bromine,chlorine, or fluorine;

R and R¹ are the same or different and are selected from hydrogen;amino; halogen (selected from chlorine, bromine, fluorine or iodine); or--NR² R³ ;

and when R or R¹ =--NR² R³ and R² =methyl or ethyl;

R³ =methyl or ethyl,

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ is selected from R⁴ (CH₂)_(n) CO-- or R^(4') (CH₂)_(n) SO₂ --;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=0,

R⁴ is selected from hydrogen; straight or branched (C₁ -C₂)alkyl groupselected from methyl or ethyl; a heterocycle group selected from a fivemembered aromatic or saturated ring with one N, O, or S heteroatomoptionally having a benzo or pyrido ring fused thereto: ##STR80##

    Z=N, O, S or Se

such as furanyl or thienyl, or a five membered aromatic ring with two N,O or S heteroatoms optionally having a benzo or pyrido ring fusedthereto: ##STR81##

    Z or Z.sup.1 =N, O, S or Se

such as pyrazolyl, benzimidazolyl or thiazolyl; (C₁ -C₄)alkoxy groupsuch as allyloxy, methoxy, ethoxy, n-propoxy, n-butoxy or tert-butoxy;C₆ -aryloxy group is selected from phenoxy or substituted phenoxy(substitution selected from halo, (C₁ -C₄)alkyl); (C₇ -C₁₀)aralkyloxygroup such as benzyloxy, 1-phenylethyloxy or 2-phenylethyloxy;α-aminomethoxycarbonyl; or halomethoxycarbonyl;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=1-4,

R⁴ is selected from hydrogen; (C₁ -C₂)alkyl group selected from methylor ethyl; (C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl orβ-naphthyl;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=0,

R^(4') is selected from straight or branched (C₁ -C₂)alkyl groupselected from methyl or ethyl; (C₆ -C₁₀)aryl group selected from phenyl,α-naphthyl or β-naphthyl;

R⁵ is selected from hydrogen; straight or branched (C₁ -C₃)alkyl groupselected from methyl, ethyl, n-propyl or 1-methylethyl;

R⁶ is selected from hydrogen; straight or branched (C₁ -C₃)alkyl groupselected from methyl, ethyl, n-propyl or 1-methylethyl; with the provisothat R⁵ and R⁶ cannot both be hydrogen;

or R⁵ and R⁶ taken together are --(CH₂)₂ W(CH₂)₂ --, wherein W isselected from (CH₂)_(n) and n=0-1, --NH, --N(C₁ -C₃)alkyl straight orbranched!, --N(C₁ -C₄)alkoxy, oxygen, sulfur or substituted congenersselected from (L or D)proline, ethyl(L or D)prolinate, morpholine,pyrrolidine or piperidine; and the pharmacologically acceptable organicand inorganic salts or metal complexes.

Also included in the present invention are compounds useful asintermediates for producing the above compounds of formula I and II.Such intermediate compounds include those having the formula III and IV:##STR82## wherein:

Y is selected from --N₂ ⁺ Cl⁻ or --N₃ ;

R or R¹ is selected from nitro; amino; halogen (selected from chlorine,bromine, fluorine or iodine); cyano; hydroxy; or --NR ² R³ ;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl or 1,1-dimethylethyl;

and when R² =methyl or ethyl,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or2-methylpropyl;

and when R² =n-propyl,

R³ =n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or 2-methylpropyl;

and when R² =1-methylethyl,

R³ =n-butyl, 1-methylpropyl or 2-methylpropyl;

and when R² =n-butyl,

R³ =n-butyl, 1-methylpropyl or 2-methylpropyl;

and when R² =1-methylpropyl,

R³ =2-methylpropyl;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ is selected from R⁴ (CH₂)_(n) CO-- or R^(4') (CH₂)_(n) SO₂ --;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=0,

R⁴ is selected from hydrogen; amino; hydroxyamino; straight or branchedmono(C₁ -C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl(ethyl)amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!-hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)-alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; azaheterocyclic groupselected from 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl),4-(1,2,4-triazolyl), 1-tetrazolyl, or 2-tetrazolyl; (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; (C₇-C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl orphenylpropylamino; straight or branched (C₁ -C₄)alkyl group selectedfrom methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl or 1,1-dimethylethyl; (C₃ -C₆)cycloalkyl group selectedfrom cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; substituted (C₃-C₆)cycloalkyl group (substitution selected from (C₁ -C₃)alkyl, cyano,amino or (C₁ -C₃)acyl); (C₆ -C₁₀)aryl group selected from phenyl,α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl group (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl; α-hydroxy(C₁ -C₃)alkyl group selected from hydroxymethyl,α-hydroxyethyl, α-hydroxy-1-methylethyl or α-hydroxypropyl;α-mercapto(C₁ -C₃)alkyl group selected from mercaptomethyl,α-mercaptoethyl, α-mercapto-1-methylethyl or α-mercaptopropyl; halo(C₁-C₃)alkyl group such as bromomethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-bromoethyl or2-iodoethyl; a heterocycle group selected from a five membered aromaticor saturated ring with one N, O, S or Se heteroatom optionally having abenzo or pyrido ring fused thereto: ##STR83##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR84##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR85## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2 , 3-dioxo-1-piperazinyl,4-methyl-2, 3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; acyl or haloacyl groupselected from acetyl, propionyl, chloroacetyl, trifluoroacetyl, (C₃-C₆)cycloalkylcarbonyl such as cyclopropylcarbonyl, cyclobutylcarbonyl,cyclopentylcarbonyl, cyclohexylcarbonyl,(2,3-dimethylcyclopropyl)carbonyl, (1,2-dimethylcyclopropyl)carbonyl,(2-ethylcyclopropyl)carbonyl, (2-methylcyclopentyl)carbonyl or(3-ethylcyclobutyl)carbonyl, (C₆ -C₁₀)aroyl selected from benzoyl ornaphthoyl, halo substituted (C₆ -C₁₀)aroyl such as pentafluorobenzoyl,4-chlorobenzoyl, 3-bromobenzoyl or 3,4-difluorobenzoyl, (C₁-C₄)alkylbenzoyl such as 4-toluoyl, 2-toluoyl or4-(1-methylethyl)benzoyl, or (heterocycle)carbonyl, the heterocycleselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom optionally having a benzo or pyrido ring fusedthereto: ##STR86##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR87##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR88## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁ -C₃)alkylthiopyridazinyl, or a six membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom such as2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; (C₁ -C₄)alkoxycarbonylgroup selected from methoxycarbonyl, ethoxycarbonyl, straight orbranched propoxylcarbonyl, straight or branched butoxycarbonyl orallyloxycarbonyl; vinyl or substituted vinyl group substitution selectedfrom (C₁ -C₃)alkyl group, halogen, (C₆ -C₁₀)aryl group selected fromphenyl, α-naphthyl, β-naphthyl, substituted (C₆ -C₁₀)aryl group(substitution selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃) alkyl,nitro, amino, cyano, (C₁ -C₄) alkoxycarbonyl, (C₁ -C₃)alkylamino orcarboxy), halo-(C₁ -C₃)alkyl group such as bromomethyl, fluoromethyl,difluoromethyl, trifluoromethyl., chloromethyl, dichloromethyl,trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-bromoethyl 5 or 2-iodoethyl, a heterocycle group selected from a fivemembered aromatic or saturated ring with one N, O, S or Se heteroatomoptionally having a benzo or pyrido ring fused thereto: ##STR89##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl!; (C₁ -C₄)alkoxygroup such as allyloxy, methoxy, ethoxy, n-propoxy, n-butoxy ortert-butoxy; C₆ -aryloxy group selected from phenoxy or substitutedphenoxy (substitution selected from halo, (C₁ -C₄)alkyl, nitro, cyano,thiol, amino, carboxy, di(C₁ -C₃)alkylamino); (C₇ -C₁₀)aralkyloxy groupsuch as benzyloxy, 1-phenylethyloxy or 2-phenylethyloxy; vinyloxy orsubstituted vinyloxy group (substitution selected from (C₁ -C₄)alkyl,cyano, carboxy, or (C₆ -C₁₀)aryl selected from phenyl, α-naphthyl orβ-naphthyl); R^(a) R^(b) amino(C₁ -C₄)alkoxy group, wherein R^(a) R^(b)is a straight or branched (C₁ -C₄)alkyl selected from methyl, ethyl,n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or1,1-dimethylethyl or R^(a) R^(b) is (CH₂)_(n), n=2-6, or --(CH₂)₂W(CH₂)₂ -- wherein W is selected from --N(C₁ -C₃)alkyl straight orbranched!, --NH, --NOB B is selected from hydrogen or (C₁ -C₃)alkyl!, Oor S; or R^(a) R^(b) aminoxy group, wherein R^(a) R^(b) is a straight orbranched (C₁ -C₄)alkyl selected from methyl, ethyl, n-propyl.,1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R^(a) R^(b)is (CH₂)_(n), n=2-6, or --(CH₂)₂ W(CH₂)₂ -- wherein W is selected from--N(C₁ -C₃)alkyl straight or branched!, --NH, --NOB B is selected fromhydrogen or (C₁ -C₃)alkyl!, O or S;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=1-4,

R⁴ is selected from hydrogen; straight or branched (C₁ -C₄)alkyl groupselected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; (C₃ -C₆)cycloalkylgroup selected from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;substituted (C₃ -C₆)cycloalkyl group (substitution selected from (C₁-C₃)alkyl, cyano, amino or (C₁ -C₃)acyl); (C₆ -C₁₀)aryl group selectedfrom phenyl, α-naphthyl or β-naphthyl; substituted(C₆ -C₁₀)aryl group(substitution selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl,nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino orcarboxy); (C₇ -C₉)aralkyl group such as benzyl, 1-phenylethyl,2-phenylethyl or phenylpropyl; acyloxy or haloacyloxy group, selectedfrom acetyl, propionyl, chloroacetyl, trichloroacetyl, (C₃-C₆)cycloalkylcarbonyl, (C₆ -C₁₀)aroyl selected from benzoyl ornaphthoyl, halo substituted (C₆ -C₁₀)aroyl such as pentafluorobenzoyl,4-chlorobenzoyl, 3-bromobenzoyl or 3,4-difluorobenzoyl, (C₁-C₄)alkylbenzoyl such as 4-toluoyl, 2-toluoyl or4-(1-methylethyl)benzoyl, (heterocycle)carbonyl, the heterocycleselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom optionally having a benzo or pyrido ring fusedthereto: ##STR90##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR91##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR92## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2, 3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; (C₁ -C₄)alkoxy group suchas allyloxy, methoxy, ethoxy, n-propoxy,n-butoxy or tert-butoxy; C₆-aryloxy group selected from phenoxy or substituted phenoxy(substitution selected from halo, (C₁ -C₄)alkyl, nitro, cyano, thiol,amino, carboxy, di-(C₁ -C₃)alkylamino); (C₇ -C 10)aralkyloxy group suchas benzyloxy, 1-phenylethyloxy or 2-phenylethyloxy; (C₁ -C₃)alkylthiogroup selected from methylthio, ethylthio, propylthio or allylthio; C6-arylthio group selected from phenylthio or substituted phenylthio(substitution selected from halo, (C₁ -C₄)alkyl, nitro, cyano, thiol,amino, carboxy, di-(C₁ -C₃)alkylamino); C₆ -arylsulfonyl group selectedfrom phenylsulfonyl or substituted phenylsulfonyl (substitution selectedfrom halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano,(C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₈)aralkylthio group such as benzylthio, 1-phenylethylthio or2-phenylethylthio; a heterocycle group selected from a five memberedaromatic or saturated ring with one N, O, S or Se heteroatom optionallyhaving a benzo or pyrido ring fused thereto: ##STR93##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR94##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR95## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; hydroxy group; mercaptogroup; α-hydroxy(C₁ -C₃)alkyl group selected from hydroxymethyl,α-hydroxyethyl or α-hydroxy-1-methylethyl or α-hydroxypropyl; halo-(C₁-C₃)alkyl group such as bromomethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-bromoethyl or2-iodoethyl; acyl or haloacyl group selected from acetyl, propionyl,chloroacetyl, trifluoroacetyl, (C₃ -C₆)cycloalkylcarbonyl, (C₆-C₁₀)aroyl selected from benzoyl or naphthoyl, halo substituted (C₆-C₁₀)aroyl such as pentafluorobenzoyl, 4-chlorobenzoyl, 3-bromobenzoyl,3,4-difluorobenzoyl, (C₁ -C₄)alkylbenzoyl such as 4-toluoyl, 2-toluoylor 4-(1-methylethyl)benzoyl, or (heterocycle)carbonyl, the heterocycleselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom optionally having a benzo or pyrido ring fusedthereto: ##STR96##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR97##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR98## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; (C₁ -C₄)alkoxycarbonylgroup selected from methoxycarbonyl, ethoxycarbonyl, straight orbranched propoxycarbonyl, allyloxycarbonyl or straight or branchedbutoxycarbonyl; R^(a) R^(b) amino(C₁ -C₄)alkoxy group, wherein R^(a)R^(b) is a straight or branched (C₁ -C₄)alkyl selected from methyl,ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or2-methylpropyl or R^(a) R^(b) is (CH₂)_(n), n=2-6, or --(CH₂)₂ W(CH₂)₂-- wherein W is selected from --N(C₁ -C₃)alkyl straight or branched!,--NH, --NOB B is selected from hydrogen or (C₁ -C₃)alkyl!, O or S; orR^(a) R^(b) aminoxy group, wherein R^(a) R^(b) is a straight or branched(C₁ -C₄)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl,n-butyl, 1-methylpropyl, or 2-methylpropyl or R^(a) R^(b) is (CH₂)_(n),n=2-6, or --(CH₂)₂ W(CH₂)₂ -- wherein W is selected from --N(C₁-C₃)alkyl straight or branched!, --NH, --NOB B is selected from hydrogenor (C₁ -C₃)alkyl!, O or S;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=2-4,

R⁴ is selected from amino; hydroxyamino; straight or branched mono(C₁-C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl (ethyl) amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl orl-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo- 2.1.1!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!-oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; azaheterocyclic groupselected from 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl),4-(1,2,4-triazolyl), 1-tetrazolyl, or 2-tetrazolyl; (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; (C₇ -C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl, α-phenylethyl,(2-naphthyl)methyl, (1-naphthyl)methyl or phenylpropylamino; (C₁-C₄)alkoxycarbonylamino group selected from tert-butoxycarbonylamino,allyloxycarbonylamino, methoxycarbonylamino, ethoxycarbonylamino orpropoxycarbonylamino;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=0,

R⁴ is selected from amino; hydroxyamino; straight or branched mono(C₁-C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl (ethyl) amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo- 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; (C₇ -C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl orphenylpropylamino; straight or branched (C₁ -C₄)alkyl group selectedfrom methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl or 1,1-dimethylethyl; (C₃ -C₆) cycloalkyl group selectedfrom cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; substituted (C₃-C₆)cycloalkyl group (substitution selected from (C₁ -C₃)alkyl, cyano,amino or (C₁ -C₃)acyl); (C₆ -C₁₀)aryl group selected from phenyl,α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl group (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group such as benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl; halo(C₁ -C₃)alkyl group such as bromomethyl, fluoromethyl,difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl,trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 2-bromoethyl or2-iodoethyl; a heterocycle group selected from a five membered aromaticor saturated ring with one N, O, S or Se heteroatom optionally having abenzo or pyrido ring fused thereto: ##STR99##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR100##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR101## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)-alkoxycarbonyl, 15 (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl) such as γ-butyrolactam, γ-butyrolactone, imidazolidinoneor N-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; R^(a) R^(b) amino-(C₁-C₄)alkoxy group, wherein R^(a) R^(b) is a straight or branched (C₁-C₄)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, or 2-methylpropyl or R^(a) R^(b) is (CH₂)_(n), n=2-6, or--(CH₂)₂ W(CH₂)₂ -- wherein W is selected from --N(C₁ -C₃)alkyl straightor branched!, --NH, --NOB B is selected from hydrogen or (C₁ -C₃)alkyl!,O or S; or R^(a) R^(b) aminoxy group, wherein R^(a) R^(b) is a straightor branched (C₁ -C₄)alkyl selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R^(a) R^(b)is (CH₂)_(n), n=2-6, or --(CH₂)₂ W(CH₂)₂ -- wherein W is selected from--N(C₁ -C₃)alkyl straight or branched!, --NH, --NOB B is selected fromhydrogen or (C₁ -C₃)alkyl!, O or S;

and when R³ =R^(4') (CH₂)_(n) SO₂ and n=1-4,

R^(4') is selected from hydrogen; amino; straight or branched (C₁-C₄)alkyl group selected from methyl, ethyl, n-propyl, 1-methylethyl,n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; (C₁-C₄)carboxyalkyl group; (C₃ -C₆)cycloalkyl group selected fromcyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; substituted (C₃-C₆)cycloalkyl group (substitution selected from (C₁ -C₃)alkyl, cyano,amino or (C₁ -C₃)acyl); (C₆ -C₁₀)aryl group selected from phenyl,α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl group (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl; (C₁ -C₄)alkoxy group such as allyloxy, methoxy, ethoxy,n-propoxy or tert-butoxy; C₆ -aryloxy group selected from phenoxy orsubstituted phenoxy (substitution selected from halo, (C₁ -C₃)alkyl,nitro, cyano, thiol, amino, carboxy, di-(C₁ -C₃)alkylamino); (C₇-C₁₀)aralkyloxy group such as benzyloxy, 1-phenylethyloxy or2-phenylethyloxy; R^(a) R^(b) amino(C₁ -C₄)alkoxy group, wherein R^(a)R^(b) is a straight or branched (C₁ -C₄)alkyl selected from methyl,ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or2-methylpropyl or R^(a) R^(b) is (CH₂)_(n), n=2-6, or --(CH₂)₂ W(CH₂)₂-- wherein W is selected from --N(C₁ -C₃)alkyl straight or branched!,--NH, --NOB B is selected from hydrogen or (C₁ -C₃)alkyl!, O or S; orR^(a) R^(b) aminoxy group, wherein R^(a) R^(b) is a straight or branched(C₁ -C₄)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl,n-butyl, 1-methylpropyl, or 2-methylpropyl or R^(a) R^(b) is (CH₂)_(n),n=2-6, or --(CH₂)₂ W(CH₂)₂ -- wherein W is selected from --N(C₁-C₃)alkyl straight or branched!, --NH, --NOB B is selected from hydrogenor (C₁ -C₃)alkyl!, O or S; (C₁ -C₃)alkylthio group selected frommethylthio, ethylthio or n-propylthio; C₆ -arylthio group selected fromphenylthio or substituted phenylthio (substitution selected from halo,(C₁ -C₃)alkyl, nitro, cyano, thiol, amino, carboxy, di-(C₁-C₃)alkylamino); (C₇ -C₈)aralkylthio group such as benzylthio,1-phenylethylthio or 2-phenylethylthio; a heterocycle group selectedfrom a five membered aromatic or saturated ring with one N, O, S or Seheteroatom optionally having a benzo or pyrido ring fused thereto:##STR102##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR103##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR104## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)-alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2, 3-dioxo-1-piperazinyl, 4-methyl-2, 3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; hydroxy group; mercaptogroup; halo(C₁ -C₃)alkyl group such as bromomethyl, fluoromethyl,difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl,trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 2-bromoethyl or2-iodoethyl; acyl or haloacyl group selected from acetyl, propionyl,chloroacetyl, trifluoroacetyl, (C₃ -C₆) cycloalkylcarbonyl, (C₆-C₁₀)aroyl selected from benzoyl or naphthoyl, halo substituted (C₆-C₁₀)aroyl such as pentafluorobenzoyl, 4-chlorobenzoyl, 3-bromobenzoylor 3,4-difluorobenzoyl, (C₁ -C₄)alkylbenzoyl such as 4-toluoyl,2-toluoyl or 4-(1-methylethyl)benzoyl, or (heterocycle)carbonyl, theheterocycle selected from a five membered aromatic or saturated ringwith one N, O, S or Se heteroatom optionally having a benzo or pyridoring fused thereto: ##STR105##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR106##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR107## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl) such as γ-butyrolactam, γ-butyrolactone, imidazolidinoneor N-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; (C₁ -C₄)alkoxycarbonylgroup selected from methoxycarbonyl, ethoxycarbonyl, straight orbranched propoxycarbonyl, allyloxycarbonyl or straight or branchedbutoxycarbonyl; and the pharmacologically acceptable organic andinorganic salts or metal complexes.

Preferred compounds are compounds according to the above formula III andIV in which Y is selected from --N₂ ⁺ Cl⁻ or --N₃ ;

R and R¹ are the same or different and are selected from hydrogen;nitro; amino; halogen (selected from chlorine, bromine, fluorine oriodine); cyano; hydroxy or --NR² R³ ;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl or 1,1-dimethylethyl;

and when R² =methyl or ethyl,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or2-methylpropyl;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ is selected from R⁴ (CH₂)_(n) CO-- or R^(4') (CH₂)_(n) SO₂ --;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=0,

R⁴ is selected from hydrogen; amino; hydroxyamino; straight or branchedmono(C₁ -C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl(ethyl)amino, thyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁ -C₄)-alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; azaheterocyclic groupselected from 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl),4-(1,2,4-triazolyl), 1-tetrazolyl, or 2-tetrazolyl; (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; (C₇ -C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl orphenylpropylamino; straight or branched (C₁ -C₃)alkyl group selectedfrom methyl, ethyl, n-propyl or 1-methylethyl; (C₃ -C₆)cycloalkyl groupselected from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;substituted (C₃ -C₆)cycloalkyl group (substitution selected from (C₁-C₃)alkyl, cyano, amino or (C₁ -C₃)acyl); (C₆ -C₁₀)aryl group selectedfrom phenyl, α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl group(substitution selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl,nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino orcarboxy); α-hydroxy(C₁ -C₃)alkyl group selected from hydroxymethyl,α-hydroxyethyl, α-hydroxy-1-methylethyl or α-hydroxypropyl; halo-(C₁-C₃)alkyl group such as bromomethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-bromoethyl or2-iodoethyl; a heterocycle group selected from a five membered aromaticor saturated ring with one N, O, S or Se heteroatom optionally having abenzo or pyrido ring fused thereto: ##STR108##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR109##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR110## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; acyl or haloacyl groupselected from acetyl, propionyl, chloroacetyl, trifluoroacetyl, (C₃ -C₆)cycloalkylcarbonyl such as cyclopropylcarbonyl, cyclobutylcarbonyl,cyclopentylcarbonyl, cyclohexylcarbonyl,(2,3-dimethylcyclopropyl)carbonyl, (1,2-dimethylcyclopropyl)carbonyl,(2-ethylcyclopropyl)carbonyl, (2-methylcyclopentyl)carbonyl or(3-ethylcyclobutyl)carbonyl, (C₆ -C₁₀)aroyl selected from benzoyl ornaphthoyl, halo substituted (C₆ -C₁₀)aroyl such as pentafluorobenzoyl,4-chlorobenzoyl, 3-bromobenzoyl or 3,4-difluorobenzoyl, (C₁-C₄)alkylbenzoyl such as 4-toluoyl, 2-methyltoluoyl or4-(1-methylethyl)benzoyl, or (heterocycle)carbonyl, the heterocycleselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom optionally having a benzo or pyrido ring fusedthereto: ##STR111##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR112##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR113## A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, heteroatoms and an adjacent appended O heteroatom such as2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; (C₁ -C₄) alkoxycarbonylgroup selected from methoxycarbonyl, ethoxycarbonyl, straight orbranched propoxylcarbonyl, straight or branched butoxycarbonyl orallyloxycarbonyl; vinyl or substituted vinyl group substitution selectedfrom (C₁ -C₃)alkyl group, halogen, (C₆ -C₁₀)aryl group selected fromphenyl, α-naphthyl, β-naphthyl, substituted (C₆ -C₁₀)aryl group(substitution selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl,nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino orcarboxy), halo(C₁ -C₃)alkyl group such as bromomethyl, fluoromethyl,difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl,trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-bromoethyl or 2-iodoethyl, a heterocycle group selected from a fivemembered aromatic or saturated ring with one N, O, S or Se heteroatomoptionally having a benzo or pyrido ring fused thereto: ##STR114##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, or benzothienyl!; (C₁ -C₄)alkoxy group suchas allyloxy, methoxy, ethoxy, n-propoxy, n-butoxy or tert-butoxy; C₆-aryloxy group selected from phenoxy or substituted phenoxy(substitution selected from halo, (C₁ -C₄)alkyl, nitro, cyano, thiol,amino, carboxy, di(C₁ -C₃)alkylamino); (C₇ -C₁₀)aralkyloxy group such asbenzyloxy, 1-phenylethyloxy or 2-phenylethyloxy; vinyloxy or substitutedvinyloxy group (substitution selected from (C₁ -C₄)alkyl, cyano,carboxy, or (C₆ -C₁₀)aryl selected from phenyl, α-naphthyl orβ-naphthyl);

R^(a) R^(b) amino(C₁ -C₄)alkoxy group, wherein R^(a) R^(b) is a straightor branched (C₁ -C₄)alkyl selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R^(a) R^(b)is (CH₂)_(n), n=2-6, or --(CH₂)₂ W(CH₂)₂ -- wherein W is selected from--N(C₁ -C₃)alkyl straight or branched), --NH, --NOB B is selected fromhydrogen or (C₁ -C₃)alkyl!, O or S; or R^(a) R^(b) aminoxy group,wherein R^(a) R^(b) is a straight or branched (C₁ -C₄)alkyl selectedfrom methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or2-methylpropyl or R^(a) R^(b) is (CH₂)_(n), n=2-6, or --(CH₂)₂ W(CH₂)₂-- wherein W is selected from --N(C₁ -C₃)alkyl straight or branched!,--NH, --NOB (B is selected from hydrogen or (C₁ -C₃)alkyl!, O or S;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=1-4,

R⁴ is selected from hydrogen; (C₁ -C₃)alkyl group selected from methyl,ethyl, n-propyl or 1-methylethyl; (C₆ -C₁₀)aryl group selected fromphenyl, α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl group(substitution selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl,nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino orcarboxy); acyloxy or haloacyloxy group, selected from acetyl, propionyl,chloroacetyl, trichloroacetyl, (C₃ -C₆) cycloalkylcarbonyl, (C₆-C₁₀)aroyl selected from benzoyl or naphthoyl, halo substituted (C₆-C₁₀)aroyl such as pentafluorobenzoyl, 4-chlorobenzoyl, 3-bromobenzoylor 3,4-difluorobenzoyl, (C₁ -C₄)alkylbenzoyl such as 4-toluoyl,2-toluoyl, 4-(1-methylethyl)benzoyl or (heterocycle)carbonyl, theheterocycle selected from a five membered aromatic or saturated ringwith one N, O, S or Se heteroatom optionally having a benzo or pyridoring fused thereto: ##STR115##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR116##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR117## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl, or a six membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl; (C₁ -C₄)alkoxy group such as allyloxy, methoxy,ethoxy, n-propoxy, n-butoxy or tert-butoxy; R^(a) R^(b) amino(C₁-C₄)alkoxy group, wherein R^(a) R^(b) is a straight or branched (C₁-C₄)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, or 2-methylpropyl or R^(a) R^(b) is (CH₂)_(n), n=2-6, or--(CH₂)₂ W(CH₂)₂ -- wherein W is selected from --N(C₁ -C₃)alkyl straightor branched!, --NH, --NOB B is selected from hydrogen or (C₁ -C₃)alkyl!,O or S; or R^(a) R^(b) aminoxy group, wherein R^(a) R^(b) is a straightor branched (C₁ -C₄)alkyl selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R^(a) R^(b)is (CH₂)_(n), n=2-6, or --(CH₂)₂ W(CH₂)₂ -- wherein W is selected from--N(C₁ -C₃)alkyl straight or branched!, --NH, --NOB B is selected fromhydrogen or (C₁ -C₃)alkyl!, O or S; C₆ -aryloxy group selected fromphenoxy or substituted phenoxy (substitution selected from halo, (C₁-C₄)alkyl, nitro, cyano, thiol, amino, carboxy, di-(C₁ -C₃)alkylamino);(C₁ -C₃)alkylthio group selected from methylthio, ethylthio, propylthioor allylthio; C₆ -arylthio group selected from phenylthio or substitutedphenylthio (substitution selected from halo, (C₁ -C₄)alkyl, nitro,cyano, thiol, amino, carboxy, di-(C₁ -C₃)alkylamino);

C₆ -arylsulfonyl group selected from phenylsulfonyl or substitutedphenylsulfonyl (substitution selected from halo, (C₁ -C₄)alkoxy,trihalo(C₁ -C₃) alkyl, nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁-C₃)alkylamino or carboxy); a heterocycle group selected from a fivemembered aromatic or saturated ring with one N, O, S or Se heteroatomoptionally having a benzo or pyrido ring fused thereto: ##STR118##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR119##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR120## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl, or a six membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl; hydroxy group; α-hydroxy(C₁ -C₃)alkyl groupselected from hydroxymethyl, α-hydroxyethyl, α-hydroxy-1-methylethyl orα-hydroxypropyl; halo(C₁ -C₃)alkyl group such as bromomethyl,fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl,dichloromethyl, trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl,2,2,2-trifluoroethyl, 2-bromoethyl or 2-iodoethyl; acyl or haloacylgroup selected from acetyl, propionyl, chloroacetyl, trifluoroacetyl,(C₃ -C₆)cycloalkylcarbonyl, (C₆ -C₁₀)aroyl selected from benzoyl ornaphthoyl, halo substituted (C₆ -C₁₀)aroyl such as pentafluorobenzoyl,4-chlorobenzoyl, 3-bromobenzoyl or 3,4-difluorobenzoyl, (C₁-C₄)alkylbenzoyl such as 4-toluoyl, 2-toluoyl, or4-(1-methylethyl)benzoyl, or (heterocycle)carbonyl, the heterocycleselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom optionally having a benzo or pyrido ring fusedthereto: ##STR121##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR122##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR123## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl) such as γ-butyrolactam, γ-butyrolactone, imidazolidinoneor N-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl, or a six membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=2-4,

R⁴ is selected from amino; hydroxyamino; straight or branched mono(C₁-C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl(ethyl)amino, ethyl-(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!-oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; azaheterocyclic groupselected from 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl),4-(1,2,4-triazolyl), 1-tetrazolyl, or 2-tetrazolyl; (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; (C₇-C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl orphenylpropylamino; (C₁ C₄)alkoxycarbonylamino group selected fromtert-butoxycarbonylamino, allyloxycarbonylamino, methoxycarbonylamino,ethoxycarbonylamino or propoxycarbonylamino;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=0,

R^(4') is selected from amino; hydroxyamino; straight or branchedmono(C₁ -C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl(ethyl)amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; (C₇ -C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl orphenylpropylamino; straight or branched (C₁ -C₃)alkyl group selectedfrom methyl, ethyl, n-propyl or 1-methylethyl; (C₆ -C₁₀)aryl groupselected from phenyl, α-naphthyl or β-naphthyl; substituted (C₆-C₁₀)aryl group (substitution selected from halo, (C₁ -C₄)alkoxy,trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁ -C₄) alkoxycarbonyl, (C₁-C₃)alkylamino or carboxy); a heterocycle group selected from a fivemembered aromatic or saturated ring with one N, O, S or Se heteroatomoptionally having a benzo or pyrido ring fused thereto: ##STR124##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR125##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR126## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄) alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or a six membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=1-4

R^(4') is selected from hydrogen; amino; straight or branched (C₁-C₃)alkyl group selected from methyl, ethyl, n-propyl or 1-methylethyl;(C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl or β-naphthyl;substituted (C₆ -C₁₀)aryl group (substitution selected from halo, (C₁-C₄)alkoxy, trihalo (C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃) alkylamino or carboxy); (C₁ -C₄)alkoxygroup such as allyloxy, methoxy, ethoxy, n-propoxy, n-butoxy, iso-butoxyor tert-butoxy; C₆ -aryloxy group selected from phenoxy or substitutedphenoxy (substitution selected from halo, (C₁ -C₄)alkyl, nitro cyano,thiol, amino, carboxy, di-(C₁ -C₃)alkylamino; (C₇ -C₁₀)aralkyloxy groupsuch as benzyloxy, 1-phenylethyloxy or 2-phenylethyloxy; (C₁-C₄)carboxyalkyl group; and the pharmacologically acceptable organic andinorganic salts or metal complexes.

Particularly preferred compounds are compounds according to the aboveformula III and IV in which Y is selected from --N₂ ⁺ Cl⁻ or --N₃ ;

R and R¹ are the same or different and are selected from hydrogen;nitro; amino; halogen (selected from chlorine, bromine, fluorine oriodine); cyano; hydroxy; or --NR² R³ ;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl or 1,1-dimethylethyl; and when R² =methyl or ethyl,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or2-methylpropyl;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ is selected from R⁴ (CH₂)_(n) CO-- or R^(4') (CH₂)_(n) SO₂ --;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=0,

R⁴ is selected from hydrogen; amino; hydroxyamino; straight or branchedmono(C₁ -C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,1-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl(ethyl)amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!-hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo-2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; azaheterocyclic groupselected from 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl),4-(1,2,4-triazolyl), 1-tetrazolyl, or 2-tetrazolyl; (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; (C₇-C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl orphenylpropylamino; straight or branched (C₁ -C₃)alkyl group selectedfrom methyl, ethyl, n-propyl or 1-methylethyl; (C₃ -C₆)cycloalkyl groupselected from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;substituted (C₃ -C₆)cycloalkyl group (substitution selected from (C₁-C₃)alkyl, cyano, amino or (C₁ -C₃)acyl); (C₆ -C₁₀)aryl group selectedfrom phenyl, α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl group(substitution selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl,nitro, amino, cyano, (C₁ -C₄)-alkoxycarbonyl, (C₁ -C₃)alkylamino orcarboxy); α-hydroxy(C₁ -C₃)alkyl group selected from hydroxymethyl,α-hydroxyethyl, α-hydroxy-1-methylethyl or α-hydroxypropyl; halo(C₁-C₃)alkyl group such as bromomethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-bromoethyl or2-iodoethyl; a heterocycle group selected from a five membered aromaticor saturated ring with one N, O, S or Se heteroatom optionally having abenzo or pyrido ring fused thereto: ##STR127##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR128##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR129## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl, or a six membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom such as 2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl; acyl or haloacyl group selected from acetyl,propionyl, chloroacetyl, trifluoroacetyl, (C₃ -C₆)cycloalkylcarbonylsuch as cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl,cyclohexylcarbonyl, (2,3-dimethylcyclopropyl)carbonyl,(1,2-dimethylcyclopropyl)carbonyl, (2-ethylcyclopropyl)carbonyl,(2-methylcyclopentyl)carbonyl or (3-ethylcyclobutyl)carbonyl, (C₆-C₁₀)aroyl selected from benzoyl or naphthoyl, halo substituted (C₆-C₁₀)aroyl such as pentafluorobenzoyl, 4-chlorobenzoyl, 3-bromobenzoylor 3,4-difluorobenzoyl, (C₁ -C₄)alkylbenzoyl such as 4-toluoyl,2-methylbenzoyl or 4-(1-methylethyl)benzoyl, or (heterocycle)carbonyl,the heterocycle selected from a five membered aromatic or saturated ringwith one N, O, S or Se heteroatom optionally having a benzo or pyridoring fused thereto: ##STR130##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR131##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR132## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl) such as γ-butyrolactam, γ-butyrolactone, imidazolidinoneor N-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl, or a six membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl; (C₁ -C₄)alkoxycarbonyl group selected frommethoxycarbonyl, ethoxycarbonyl, straight or branched propoxylcarbonyl,straight or branched butoxycarbonyl or allyloxycarbonyl; vinyl orsubstituted vinyl group substitution selected from (C₁ -C₃)alkyl group,halogen, (C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl,β-naphthyl, substituted (C₆ -C₁₀)aryl group (substitution selected fromhalo, (C₁ -C₄)alkoxy, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino orcarboxy), halo(C₁ -C₃)alkyl group such as bromomethyl, fluoromethyl,difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl,trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-bromoethyl or 2-iodoethyl, a heterocycle group selected from a fivemembered aromatic or saturated ring with one N, O, S or Se heteroatomoptionally having a benzo or pyrido ring fused thereto: ##STR133##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, or benzothienyl!; (C₁ -C₄)alkoxy group suchas allyloxy, methoxy, ethoxy, n-propoxy, n-butoxy or tert-butoxy; C₆-aryloxy group selected from phenoxy or substituted phenoxy(substitution selected from halo, (C₁ -C₄)alkyl); (C₇ -C₁₀)aralkyloxygroup such as benzyloxy, 1-phenylethyloxy or 2-phenylethyloxy;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=1-4,

R⁴ is selected from hydrogen; (C₁ -C₃)alkyl group selected from methyl,ethyl, n-propyl or 1-methylethyl; (C₆ -C₁₀)aryl group selected fromphenyl, α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl group(substitution selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl,nitro, amino, cyano, (C₁ -C₄) alkoxycarbonyl, (C₁ -C₃)alkylamino orcarboxy); acyloxy or haloacyloxy group, selected from acetyl, propionyl,chloroacetyl, trichloroacetyl, (C₃ -C₆) cycloalkylcarbonyl, (C₆-C₁₀)aroyl selected from benzoyl or naphthoyl, halo substituted (C₆-C₁₀)aroyl such as pentafluorobenzoyl, 4-chlorobenzoyl, 3-bromobenzoylor 3,4-difluorobenzoyl, (C₁ -C₄)alkylbenzoyl such as 4-toluoyl,2-toluoyl, 4-(1-methylethyl)benzoyl or (heterocycle)-carbonyl, theheterocycle selected from a five membered aromatic or saturated ringwith one N, O, S or Se heteroatom optionally having a benzo or pyridoring fused thereto: ##STR134##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR135##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR136## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl or pyrazinyl, or a sixmembered saturated ring with one or two N, O, S or Se heteroatoms and anadjacent appended O heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl; (C₁ -C₄)alkoxy group such as allyloxy, methoxy,ethoxy, n-propoxy, n-butoxy or tert-butoxy; C₆ -aryloxy group selectedfrom phenoxy or substituted phenoxy (substitution selected from halo,(C₁ -C₄)alkyl, nitro, cyano, thiol, amino, carboxy, di-(C₁-C₃)alkylamino); (C₁ -C₃)alkylthio group selected from methylthio,ethylthio, propylthio or allylthio; C₆ -arylthio group selected fromphenylthio or substituted phenylthio (substitution selected from halo,(C₁ -C₄)alkyl, nitro, cyano, thiol, amino, carboxy, di-(C₁-C₃)alkylamino); C₆ -arylsulfonyl group selected from phenylsulfonyl orsubstituted phenylsulfonyl (substitution selected from halo, (C₁-C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); a heterocycle groupselected from a five membered aromatic or saturated ring one N, O, S orSe heteroatom optionally having a benzo or pyrido ring fused thereto:##STR137##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR138##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR139## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl or pyrazinyl, or a sixmembered saturated ring with one or two N, O, S or Se heteroatoms and anadjacent appended O heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl; hydroxy group; α-hydroxy(C₁ -C₃)alkyl groupselected from hydroxymethyl, α-hydroxyethyl, α-hydroxy-1-methylethyl orα-hydroxypropyl; halo-(C₁ -C₃)alkyl group such as bromomethyl,fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl,dichloromethyl, trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl,2,2,2-trifluoroethyl, 2-bromoethyl or 2-iodoethyl; acyl or haloacylgroup selected from acetyl, propionyl, chloroacetyl, trifluoroacetyl,(C₃ -C₆) cycloalkylcarbonyl, (C₆ -C₁₀)aroyl selected from benzoyl ornaphthoyl, halo substituted (C₆ -C₁₀)aroyl such as pentafluorobenzoyl,4-chlorobenzoyl, 3-bromophenylcarbonyl or 3,4-difluorobenzoyl, (C₁ -C₄)alkylbenzoyl such as from 4-toluoyl, 2-toluoyl or4-(1-methylethyl)benzoyl, or (heterocycle)carbonyl, the heterocycleselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom optionally having a benzo or pyrido ring fusedthereto: ##STR140##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR141##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR142## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl) such as γ-butyrolactam, γ-butyrolactone, imidazolidinoneor N-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl or pyrazinyl, or a sixmembered saturated ring with one or two N, O, S or Se heteroatoms and anadjacent appended O heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=2-4,

R⁴ is selected from amino; hydroxyamino; straight or branched mono(C₁-C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl(ethyl)amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; azaheterocyclic groupselected from 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl),4-(1,2,4-triazolyl), 1-tetrazolyl, or 2-tetrazolyl; (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; (C₇-C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl) methyl, (1-naphthyl) methyl orphenylpropylamino; (C₁ -C₄)alkoxycarbonylamino group selected fromtert-butoxycarbonylamino, allyloxycarbonylamino, methoxycarbonylamino,ethoxycarbonylamino or propoxycarbonylamino;

and when R³ =R^(4') (CH₂)_(n) SO-- and n=0,

R^(4') is selected from amino; hydroxyamino; straight or branchedmono(C₁ -C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl(ethyl)amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.l!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.l!hept-2-yl and whereappropriate their diastereomers and enantiomers; azaheterocyclic groupselected from 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl),4-(1,2,4-triazolyl), 1-tetrazolyl, or 2-tetrazolyl; (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; (C₇ -C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl orphenylpropylamino; straight or branched (C₁ -C₃)alkyl group selectedfrom methyl, ethyl, n-propyl or 1-methylethyl; (C₆ -C₁₀)aryl groupselected from phenyl, α-naphthyl or β-naphthyl; substituted (C₆-C₁₀)aryl group (substitution selected from halo, (C₁ -C₄)alkoxy,trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁-C₃)alkylamino or carboxy); a heterocycle group selected from a fivemembered aromatic or saturated ring with one N, O, S or Se heteroatomoptionally having a benzo or pyrido ring fused thereto: ##STR143##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=1-4,

R^(4') is selected from hydrogen; amino; straight or branched (C₁-C₃)alkyl group selected from methyl, ethyl, n-propyl or 1-methylethyl;and the pharmacologically acceptable organic and inorganic salts ormetal complexes.

Most particularly preferred compounds are compounds according to theabove formula III and IV in which Y is selected from --N₂ ^(+Cl) ⁻ or--N₃ ;

R and R¹ are the same or different and are selected from hydrogen;nitro; amino; halogen (selected from chlorine, bromine, fluorine oriodine); cyano; hydroxy; or --NR² R³ ;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl or 1,1-dimethylethyl;

and when R² =methyl or ethyl,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or2-methylpropyl;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ selected from R⁴ (CH₂)_(n) CO-- or R^(4') (CH₂)_(n) SO₂ --;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=0,

R⁴ is selected from hydrogen; amino; hydroxyamino; straight or branchedmono(C₁ -C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.l!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl(ethyl)amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!-hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; (C₇-C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl orphenylpropylamino; straight or branched (C₁ -C₂)alkyl group selectedfrom methyl or ethyl; (C₆ -C₁₀)aryl group selected from phenyl,α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl group (substitutionselected from halo, (C₁ -C₄)alkoxy, nitro, amino); α-hydroxy (C₁-C₃)alkyl group selected from hydroxymethyl; halo(C₁ -C₃)alkyl groupsuch as bromomethyl, fluoromethyl, difluoro methyl, trifluoromethyl,chloromethyl, dichloromethyl, trichloromethyl, 2-fluoroethyl,2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-bromoethyl or 2-iodoethyl; aheterocycle group selected from a five membered aromatic or saturatedring with one N, O, S or Se heteroatom optionally having a benzo orpyrido ring fused thereto: ##STR144##

    Z=N, O, S or Se

such as indolyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 2-pyrrolinyl,tetrahydrofuranyl, furanyl, benzofuranyl, tetrahydrothienyl or thienyl,or a five membered aromatic ring with two N, O, S or Se heteroatomsoptionally having a benzo or pyrido ring fused thereto: ##STR145##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, indazolyl, thiazolyl orbenzothiazolyl; (C₁ -C₄)alkoxycarbonyl group selected frommethoxycarbonyl, ethoxycarbonyl, straight or branched propoxycarbonyl,straight or branched butoxycarbonyl or allyloxycarbonyl; vinyl orsubstituted vinyl group substitution selected from (C₁ -C₃)alkyl group,(C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl, β-naphthyl!; (C₁-C₄)alkoxy group such as allyloxy, methoxy, ethoxy, n-propoxy, n-butoxyor tert-butoxy; C₆ -aryloxy group selected from phenoxy or substitutedphenoxy (substitution selected from halo, (C₁ -C₄)alkyl); (C₇-C₁₀)aralkyloxy group such as benzyloxy, 1-phenylethyloxy or2-phenylethyloxy;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=1-4,

R⁴ is selected from hydrogen; (C₁ -C₂)alkyl group selected from methylor ethyl; (C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl orβ-naphthyl; substituted(C₆ -C₁₀)aryl group (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl); acyloxy or haloacyloxygroup, selected from acetyl, propionyl, chloroacetyl, trichloroacetyl,(C₃ -C₆) cycloalkylcarbonyl, (C₆ -C₁₀)aroyl selected from benzoyl ornaphthoyl, halo substituted (C₆ -C₁₀)aroyl such as pentafluorobenzoyl,4-chlorobenzoyl, 3-bromobenzoyl or 3,4-difluorobenzoyl, (C₁-C₄)alkylbenzoyl such as 4-toluoyl, 2-toluoyl, 4-(1-methylethyl)benzoylor (heterocycle)carbonyl, the heterocycle selected from a five memberedaromatic or saturated ring with one N, O, S or Se heteroatom optionallyhaving a benzo or pyrido ring fused thereto: ##STR146##

    Z=N, O, S or Se

such as tetrahydrofuranyl, furanyl, benzofuranyl, tetrahydrothienyl,thienyl or benzothienyl, or a five membered aromatic ring with two N, O,S or Se heteroatoms optionally having a benzo or pyrido ring fusedthereto: ##STR147##

    Z or Z.sup.1 =N, O, S or Se

such as pyrazolyl, benzimidazolyl, benzoxazolyl, indazolyl, thiazolyl orbenzothiazolyl, or a six membered aromatic ring with one or two Nheteroatoms such as pyridyl or pyridazinyl; (C₁ -C₄)alkoxy group such asallyloxy, methoxy, ethoxy, n-propoxy, n-butoxy or tert-butoxy;α-hydroxy(C₁ -C₃)alkyl group selected from hydroxymethyl,α-hydroxyethyl, α-hydroxy-1-methylethyl or α-hydroxypropyl; halo(C₁-C₃)alkyl group such as bromomethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-bromoethyl or2-iodoethyl;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=2-4,

R⁴ is selected from amino; hydroxyamino; straight or branched mono(C₁-C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl(ethyl)amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers.; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)-alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; (C₇-C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl) methyl, (1-naphthyl) methyl orphenylpropylamino; (C₁ -C₄)alkoxycarbonylamino group selected fromtert-butoxycarbonylamino, allyloxycarbonylamino, methoxycarbonylamino,ethoxycarbonylamino or propoxycarbonylamino;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=0,

R^(4') is selected from amino; straight or branched (C₁ -C₂)alkyl groupselected from methyl or ethyl; (C₆ -C₁₀)aryl group selected from phenyl,α-naphthyl or β-naphthyl;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=1-4,

R^(4') is selected from hydrogen; straight or branched (C₁ -C₂)alkylgroup selected from methyl or ethyl; and the pharmacologicallyacceptable organic and inorganic salts or metal complexes.

Compounds of special interest are compounds according to the aboveformula III and IV in which Y is --N⁺ Cl⁻ or --N₃ ;

R or R¹ are selected from nitro; amino; halogen (selected from chlorine,bromine, fluorine or iodine); cyano; hydroxy; or --NR² R³ ;

and when R or R¹ =--NR² R³ and R² =methyl or ethyl;

R³ =methyl or ethyl,

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ is selected from R⁴ (CH₂)_(n) CO-- or R^(4') (CH₂)_(n) SO₂ --;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=0,

R⁴ is selected from hydrogen; straight or branched (C₁ -C₂)alkyl groupselected from methyl or ethyl; a heterocycle group selected from a fivemembered aromatic or saturated ring with one N, O, or S heteroatomoptionally having a benzo or pyrido ring fused thereto: ##STR148##

    Z=N, O, S or Se

such as furanyl or thienyl, or a five membered aromatic ring with two N,O or S heteroatoms optionally having a benzo or pyrido ring fusedthereto: ##STR149##

    Z or Z.sup.1 =N, O, S or Se

such as pyrazolyl, benzimidazolyl or thiazolyl; (C₁ -C₄)alkoxy groupsuch as allyloxy, methoxy, ethoxy, n-propoxy, n-butoxy or tert-butoxy;C₆ -aryloxy group selected from phenoxy or substituted phenoxy(substitution selected from halo, (C₁ -C₄)alkyl); (C₇ -C₁₀)aralkyloxygroup such as benzyloxy, 1-phenylethyloxy or 2-phenylethyloxy;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=1-4,

R⁴ is selected from hydrogen; (C₁ -C₂)alkyl group selected from methylor ethyl; (C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl orβ-naphthyl;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=0,

R^(4') is selected from straight or branched (C₁ -C₂)alkyl groupselected from methyl or ethyl; (C₆ -C₁₀)aryl group selected from phenyl,α-naphthyl or β-naphthyl; and the pharmacologically acceptable organicand inorganic salts or metal complexes.

Additional intermediate compounds include those having the formula V andVI: ##STR150## wherein:

Y is selected from --N₂ ⁺ Cl⁻ or N₃ ;

X is selected from halogen or trifluoromethanesulfonyloxy; the halogenis selected from bromine, chlorine, fluorine or iodine;

R or R¹ is selected from nitro; amino; halogen (selected from chlorine,bromine, fluorine or iodine); cyano; hydroxy; or --NR² R³ ;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl or 1,1-dimethylethyl;

and when R² =methyl or ethyl,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or2-methylpropyl;

and when R² =n-propyl,

R³ =n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or 2-methylpropyl;

and when R² =1-methylethyl,

R³ =n-butyl, 1-methylpropyl or 2-methylpropyl;

and when R =n-butyl,

R³ =n-butyl, 1-methylpropyl or 2-methylpropyl;

and when R² =1-methylpropyl,

R³ =2-methylpropyl;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ is selected from R⁴ (CH₂)_(n) CO-- or R^(4') (CH₂)_(n) SO₂ --;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=0,

R⁴ is selected from hydrogen; amino; hydroxyamino; straight or branchedmono(C₁ -C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈) cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl(ethyl)amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)-azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!-hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.l!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; (C₇-C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl orphenylpropylamino; straight or branched (C₁ -C₄)alkyl group selectedfrom methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl or 1,1-dimethylethyl; (C₃ -C₆)cycloalkyl group selectedfrom cyclopropyl, cyclobutyl, cyclo-pentyl or cyclohexyl; substituted(C₃ -C₆)cycloalkyl group (substitution selected from (C₁ -C₃)alkyl,cyano, amino or (C₁ -C₃)acyl); (C₆ -C₁₀)aryl group selected from phenyl,α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl group (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)-alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl; α-hydroxy(C₁ -C₃)alkyl group selected from hydroxymethyl,α-hydroxyethyl, α-hydroxy-1-methylethyl or α-hydroxypropyl;α-mercapto(C₁ -C₃)alkyl group selected from mercaptomethyl,α-mercaptoethyl, α-mercapto-1-methylethyl or α-mercaptopropyl; halo(C₁-C₃)alkyl group such as bromomethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-bromoethyl or2-iodoethyl; a heterocycle group selected from a five membered aromaticor saturated ring with one N, O, S or Se heteroatom optionally having abenzo or pyrido ring fused thereto: ##STR151##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR152##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR153## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended 0 heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; acyl or haloacyl groupselected from acetyl, propionyl, chloroacetyl, trifluoroacetyl, (C₃-C₆)cycloalkylcarbonyl such as cyclopropylcarbonyl, cyclobutylcarbonyl,cyclopentylcarbonyl, cyclohexylcarbonyl,(2,3-dimethylcyclopropyl)carbonyl, (1,2-dimethylcyclopropyl)carbonyl,(2-ethylcyclopropyl)carbonyl, (2-methylcyclopentyl)carbonyl or(3-ethylcyclobutyl)carbonyl, (C₆ -C₁₀)aroyl selected from benzoyl ornaphthoyl, halo substituted (C₆ -C₁₀)aroyl such as pentafluorobenzoyl,4-chlorobenzoyl, 3-bromobenzoyl or 3,4-difluorobenzoyl, (C₁-C₄)alkylbenzoyl such as 4-toluoyl, 2-toluoyl or4-(1-methylethyl)benzoyl, or (heterocycle)carbonyl, the heterocycleselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom optionally having a benzo or pyrido ring fusedthereto: ##STR154##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR155##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR156## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁ -C₃)alkylthiopyridazinyl, or a six membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom such as2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; (C₁ -C₄)alkoxycarbonylgroup selected from methoxycarbonyl, ethoxycarbonyl, straight orbranched propoxylcarbonyl, straight or branched butoxycarbonyl orallyloxycarbonyl; vinyl or substituted vinyl group substitution selectedfrom (C₁ -C₃)alkyl group, halogen, (C₆ -C₁₀)aryl group selected fromphenyl, α-naphthyl, β-naphthyl, substituted (C₆ -C₁₀)aryl group(substitution selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl,nitro, amino, cyano, (C₁ -C₄) alkoxycarbonyl, (C₁ -C₃)alkylamino orcarboxy), halo(C₁ -C₃)alkyl group such as bromomethyl, fluoromethyl,difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl,trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-bromoethyl or 2-iodoethyl, a heterocycle group selected from a fivemembered aromatic or saturated ring with one N, O, S or Se heteroatomoptionally having a benzo or pyrido ring fused thereto: ##STR157##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl!; (C₁ -C₄)alkoxygroup such as allyloxy, methoxy, ethoxy, n-propoxy, n-butoxy ortert-butoxy; C₆ -aryloxy group selected from phenoxy or substitutedphenoxy (substitution selected from halo, (C₁ -C₄)alkyl, nitro, cyano,thiol, amino, carboxy, di-(C₁ -C₃)alkylamino); (C₇ -C₁₀)aralkyloxy groupsuch as benzyloxy, 1-phenylethyloxy or 2-phenylethyloxy; vinyloxy orsubstituted vinyloxy group (substitution selected from (C₁ -C₄)alkyl,cyano, carboxy, or (C₆ -C₁₀)aryl selected from phenyl, α-naphthyl orβ-naphthyl); R^(a) R^(b) amino(C₁ -C₄)alkoxy group, wherein R^(a) R^(b)is a straight or branched (C₁ -C₄)alkyl selected from methyl, ethyl,n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or1,1-dimethylethyl or R^(a) R^(b) is (CH₂)_(n), n=2-6, or --(CH₂)₂W(CH₂)₂ -- wherein W is selected from --N(C₁ -C₃)alkyl straight orbranched!, --NH, --NOB B is selected from hydrogen or (C₁ -C₃)alkyl!, Oor S; or R^(a) R^(b) aminoxy group, wherein R^(a) R^(b) is a straight orbranched (C₁ -C₄)alkyl selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R^(a) R^(b)is (CH₂)_(n) , n=2-6, or --(CH₂)₂ W(CH₂)₂ -- wherein W is selected from--N(C₁ -C₃)alkyl straight or branched!, --NH, --NOB B is selected fromhydrogen or (C₁ -C₃)alkyl!, O or S;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=1-4,

R⁴ is selected from hydrogen; straight or branched (C₁ -C₄)alkyl groupselected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; (C₃ -C₆)cycloalkylgroup selected from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;substituted (C₃ -C₆)cycloalkyl group (substitution selected from (C₁-C₃) alkyl, cyano, amino or (C₁ -C₃)acyl); (C₆ -C₁₀)aryl group selectedfrom phenyl, α-naphthyl or β-naphthyl; substituted(C₆ -C₁₀)aryl group(substitution selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl,nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃) alkylamino orcarboxy); (C₇ -C₉)aralkyl group such as benzyl, 1-phenylethyl,2-phenylethyl or phenylpropyl; acyloxy or haloacyloxy group, selectedfrom acetyl, propionyl, chloroacetyl, trichloroacetyl, (C₃-C₆)cycloalkylcarbonyl, (C₆ -C₁₀)aroyl selected from benzoyl ornaphthoyl, halo substituted (C₆ -C₁₀)aroyl such as pentafluorobenzoyl,4-chlorobenzoyl, 3-bromobenzoyl or 3,4-difluorobenzoyl, (C₁-C₄)alkylbenzoyl such as 4-toluoyl, 2-toluoyl or4-(1-methylethyl)benzoyl, (heterocycle)carbonyl, the heterocycleselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom optionally having a benzo or pyrido ring fusedthereto: ##STR158##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR159##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR160## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2, 3-dioxo-1-piperazinyl,4-methyl-2, 3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; (C₁ -C₄)alkoxy group suchas allyloxy, methoxy, ethoxy, n-propoxy, n-butoxy or tert-butoxy; C₆-aryloxy group selected from phenoxy or substituted phenoxy(substitution selected from halo, (C₁ -C₄)alkyl, nitro, cyano, thiol,amino, carboxy, di-(C₁ -C₃)alkylamino); (C₇ -C₁₀)aralkyloxy group suchas benzyloxy, 1-phenylethyloxy or 2-phenylethyloxy; (C₁ -C₃)alkylthiogroup selected from methylthio, ethylthio, propylthio or allylthio; C₆-arylthio group selected from phenylthio or substituted phenylthio(substitution selected from halo, (C₁ -C₄)alkyl, nitro, cyano, thiol,amino, carboxy, di-(C₁ -C₃)alkylamino); C₆ -arylsulfonyl group selectedfrom phenylsulfonyl or substituted phenylsulfonyl (substitution selectedfrom halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano,(C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₈)aralkylthio group such as benzylthio, 1-phenylethylthio or2-phenylethylthio; a heterocycle group selected from a five memberedaromatic or saturated ring with one N, O, S or Se heteroatom optionallyhaving a benzo or pyrido ring fused thereto: ##STR161##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR162##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR163## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; hydroxy group; mercaptogroup; α-hydroxy(C₁ -C₃)alkyl group selected from hydroxymethyl,α-hydroxyethyl or α-hydroxy-1-methylethyl or α-hydroxypropyl; halo(C₁-C₃)alkyl group such as bromomethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-bromoethyl or2-iodoethyl; acyl or haloacyl group selected from acetyl, propionyl,chloroacetyl, trifluoroacetyl, (C₃ -C₆)cycloalkylcarbonyl, (C₆-C₁₀)aroyl selected from benzoyl or naphthoyl, halo substituted (C₆-C₁₀)aroyl such as pentafluorobenzoyl, 4-chlorobenzoyl, 3-bromobenzoyl,3,4-difluorobenzoyl, (C₁ -C₄)alkylbenzoyl such as 4-toluoyl, 2-toluoylor 4-(1-methylethyl)benzoyl, or (heterocycle)carbonyl, the heterocycleselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom optionally having a benzo or pyrido ring fusedthereto: ##STR164##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR165##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR166## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; (C₁ -C₄)alkoxycarbonylgroup selected from methoxycarbonyl, ethoxycarbonyl, straight orbranched propoxycarbonyl, allyloxycarbonyl or straight or branchedbutoxycarbonyl; R^(a) R^(b) amino(C₁ -C₄)alkoxy group, wherein R^(a)R^(b) is a straight or branched (C₁ -C₄)alkyl selected from methyl,ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or2-methylpropyl or R^(a) R^(b) is (CH₂)_(n), n=2-6, or --(CH₂)₂ W(CH₂)₂-- wherein W is selected from --N(C₁ -C₃)alkyl straight or branched!,--NH, --NOB B is selected from hydrogen or (C₁ -C₃)alkyl!, O or S; orR^(a) R^(b) aminoxy group, wherein R^(a) R^(b) is a straight or branched(C₁ -C₄)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl,n-butyl, 1-methylpropyl, or 2-methylpropyl or R^(a) R^(b) is (CH₂)_(n),n=2-6, or --(CH₂)₂ W--(CH₂)₂ -- wherein W is selected from --N(C₁-C₃)alkyl straight or branched!, --NH, --NOB B is selected from hydrogenor (C₁ -C₃)alkyl!, O or S;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=2-4,

R⁴ is selected from amino; hydroxyamino; straight or branched mono(C₁-C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2)oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl(ethyl)amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!-oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁ -C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; (C₇-C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl orphenylpropylamino; (C₁ -C₄)alkoxycarbonylamino group selected fromtert-butoxycarbonylamino, allyloxycarbonylamino, methoxycarbonylamino,ethoxycarbonylamino or propoxycarbonylamino;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=0,

R^(4') is selected from amino; hydroxyamino; straight or branchedmono(C₁ -C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl(ethyl)amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino;straight or branched (C₁ -C₄)alkyl group selected from methyl, ethyl,n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or1,1-dimethylethyl; (C₃ -C₆)cycloalkyl group selected from cyclopropyl,cyclobutyl, cyclopentyl or cyclohexyl; substituted (C₃ -C₆)cycloalkylgroup (substitution selected from (C₁ -C₃)alkyl, cyano, amino or (C₁-C₃)acyl); (C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl orβ-naphthyl; substituted (C₆ -C₁₀)aryl group (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup such as benzyl, 1-phenylethyl, 2-phenylethyl or phenylpropyl;halo(C₁ -C₃)alkyl group such as bromomethyl, fluoromethyl,difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl,trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 2-bromoethyl or2-iodoethyl; a heterocycle group selected from a five membered aromaticor saturated ring with one N, O, S or Se heteroatom optionally having abenzo or pyrido ring fused thereto: ##STR167##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR168##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR169## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl) γsuch as γ-butyrolactam, γ-butyrolactone, imidazolidinoneor N-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; R^(a) R^(b) amino(C₁-C₄)alkoxy group, wherein R^(a) R^(b) is a straight or branched (C₁-C₄)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, or 2-methylpropyl or R^(a) R^(b) is (CH₂)_(n), n=2-6, or--(CH₂)₂ W(CH₂)₂ -- wherein W is selected from --N(C₁ -C₃)alkyl(straight or branched!, --NH, --NOB B is selected from hydrogen or (C₁-C₃)alkyl!, O or S; or R^(a) R^(b) aminoxy group, wherein R^(a) R^(b) isa straight or branched (C₁ -C₄)alkyl selected from methyl, ethyl,n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl orR^(a) R^(b) is (CH₂)_(n), n=2-6, or --(CH₂)₂ W(CH₂)₂ -- wherein W isselected from --N(C₁ -C₃)alkyl straight or branched!, --NH, --NOB B isselected from hydrogen or (C₁ -C₃)alkyl!, O or S;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=1-4,

R^(4') is selected from hydrogen; amino; straight or branched (C₁-C₄)alkyl group selected from methyl, ethyl, n-propyl, 1-methylethyl,n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; (C₁-C₄)carboxyalkyl group; (C₃ -C₆)cycloalkyl group selected fromcyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; substituted (C₃-C₆)cycloalkyl group (substitution selected from (C₁ -C₃)alkyl, cyano,amino or (C₁ -C₃)acyl); (C₆ -C₁₀)aryl group selected from phenyl,α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl group (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl; (C₁ -C₄)alkoxy group such as allyloxy, methoxy, ethoxy,n-propoxy or tert-butoxy; C₆ -aryloxy group selected from phenoxy orsubstituted phenoxy (substitution selected from halo, (C₁ -C₃)alkyl,nitro, cyano, thiol, amino, carboxy, di-(C₁ -C₃)alkylamino); (C₇-C₁₀)aralkyloxy group such as benzyloxy, 1-phenylethyloxy or2-phenylethyloxy; R^(a) R^(b) amino(C₁ -C₄)alkoxy group, wherein R^(a)R^(b) is a straight or branched (C₁ -C₄)alkyl selected from methyl,ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or2-methylpropyl or R^(a) R^(b) is (CH₂)_(n), n=2-6, or --(CH₂)₂ W(CH₂)₂-- wherein W is selected from --N(C₁ -C₃)alkyl straight or branched!,--NH, --NOB B is selected from hydrogen or (C₁ -C₃)alkyl!, O or S; orR^(a) R^(b) aminoxy group, wherein R^(a) R^(b) is a straight or branched(C₁ -C₄)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl,n-butyl, 1-methylpropyl, or 2-methylpropyl or R^(a) R^(b) is (CH₂)_(n),n=2-6, or --(CH₂)₂ W(CH₂)₂ -- wherein W is selected from --N(C₁-C₃)alkyl straight or branched!, --NH, --NOB B is selected from hydrogenor (C₁ -C₃)alkyl!, O or S;(C₁ -C₃)alkylthio group selected frommethylthio, ethylthio or n-propylthio; C₆ -arylthio group selected fromphenylthio or substituted phenylthio (substitution selected from halo,(C₁ -C₃)alkyl, nitro, cyano, thiol, amino, carboxy, di-(C₁-C₃)alkylamino); (C₇ -C₈)aralkylthio group such as benzylthio,1-phenylethylthio or 2-phenylethylthio; a heterocycle group selectedfrom a five membered aromatic or saturated ring with one N, O, S or Seheteroatom optionally having a benzo or pyrido ring fused thereto:##STR170##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR171##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom:##STR172## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; hydroxy group; mercaptogroup; halo(C₁ -C₃)alkyl group such as bromomethyl, fluoromethyl,difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl,trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 2-bromoethyl or2-iodoethyl; acyl or haloacyl group selected from acetyl, propionyl,chloroacetyl, trifluoroacetyl, (C₃ -C₆)cycloalkylcarbonyl, (C₆-C₁₀)aroyl selected from benzoyl or naphthoyl, halo substituted (C₆-C₁₀)aroyl such as pentafluorobenzoyl, 4-chlorobenzoyl, 3-bromobenzoylor 3,4-difluorobenzoyl, (C₁ -C₄)alkylbenzoyl such as 4-toluoyl,2-toluoyl or 4-(1-methylethyl)benzoyl, or (heterocycle)carbonyl, theheterocycle selected from a five membered aromatic or saturated ringwith one N, O, S or Se heteroatom optionally having a benzo or pyridoring fused thereto: ##STR173##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, benzothienyl or selenazolyl, or a fivemembered aromatic ring with two N, O, S or Se heteroatoms optionallyhaving a benzo or pyrido ring fused thereto: ##STR174##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl, benzothiazolyl, 3-alkyl-3H-imidazo 4,5-b!pyridylor pyridylimidazolyl, or a five membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended o heteroatom:##STR175## (A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo (C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇ -C₉)aralkylgroup selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; (C₁ -C₄)alkoxycarbonylgroup selected from methoxycarbonyl, ethoxycarbonyl, straight orbranched propoxycarbonyl, allyloxycarbonyl or straight or branchedbutoxycarbonyl; and the pharmacologically acceptable organic andinorganic salts or metal complexes.

Preferred compounds are compounds according to the above formula V andVI in which X is selected from halogen or trifluoromethanesulfonyloxy;the halogen is selected from bromine, chlorine, fluorine or iodine;

Y is selected from --N⁺ Cl⁻ or N₃ ;

R or R¹ are selected from nitro; amino; halogen (selected from chlorine,bromine, fluorine or iodine); cyano; hydroxy or --NR² R³ ;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl or 1,1-dimethylethyl;

and when R² =methyl or ethyl,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or2-methylpropyl;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ is selected from R⁴ (CH₂)_(n) CO-- or R^(4') (CH₂)_(n) SO₂ --;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=0,

R⁴ is selected from hydrogen; amino; hydroxyamino; straight or branchedmono(C₁ -C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methyl-butyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈).cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl (ethyl) amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; (C₇-C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl orphenylpropylamino; straight or branched (C₁ -C₃)alkyl group selectedfrom methyl, ethyl, n-propyl or 1-methylethyl; (C₃ -C₆)cycloalkyl groupselected from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;substituted (C₃ -C₆)cycloalkyl group (substitution selected from (C₁-C₃)alkyl, cyano, amino or (C₁ -C₃)acyl); (C₆ -C₁₀)aryl group selectedfrom phenyl, α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl group(substitution selected from halo, (C₁ -C₄)alkoxy, trihalo (C₁ -C₃)alkyl, nitro, amino, cyano, (C₁ -C₄) alkoxycarbonyl, (C₁ -C₃)alkylaminoor carboxy); α-hydroxy(C₁ -C₃)alkyl group selected from hydroxymethyl,α-hydroxyethyl, α-hydroxy-1-methylethyl or α-hydroxypropyl; halo(C₁-C₃)alkyl group such as bromomethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-bromoethyl or2-iodoethyl; a heterocycle group selected from a five membered aromaticor saturated ring with one N, O, S or Se heteroatom optionally having abenzo or pyrido ring fused thereto: ##STR176##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR177##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR178## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo (C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁ -C₃)alkylthiopyridazinyl, or a six membered saturated ring with one or twoN, O, S or Se heteroatoms and an adjacent appended O heteroatom such as2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; acyl or haloacyl groupselected from acetyl, propionyl, chloroacetyl, trifluoroacetyl, (C₃-C₆)cycloalkylcarbonyl such as cyclopropylcarbonyl, cyclobutylcarbonyl,cyclopentylcarbonyl, cyclohexylcarbonyl,(2,3-dimethylcyclopropyl)carbonyl, (1,2-dimethylcyclopropyl)carbonyl,(2-ethylcyclopropyl)carbonyl, (2-methylcyclopentyl)carbonyl or(3-ethylcyclobutyl)carbonyl, (C₆ -C₁₀)aroyl selected from benzoyl ornaphthoyl, halo substituted (C₆ -C₁₀)aroyl such as pentafluorobenzoyl,4-chlorobenzoyl, 3-bromobenzoyl or 3,4-difluorobenzoyl, (C₁-C₄)alkylbenzoyl such as 4-toluoyl, 2-methyltoluoyl or4-(1-methylethyl)benzoyl, or (heterocycle)carbonyl, the heterocycleselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom optionally having a benzo or pyrido ring fusedthereto: ##STR179##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR180##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR181## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)-alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or (C₁-C₃)alkylthiopyridazinyl, or a six membered saturated ring with one ortwo N, O, S or Se heteroatoms and an adjacent appended O heteroatom suchas 2,3-dioxo-1-piperazinyl, 4-ethyl-2,3-dioxo-1-piperazinyl,4-methyl-2,3-dioxo-1-piperazinyl, 4-cyclopropyl-2-dioxo-1-piperazinyl,2-dioxomorpholinyl or 2-dioxothiomorpholinyl; (C₁ -C₄)alkoxycarbonylgroup selected from methoxycarbonyl, ethoxycarbonyl, straight orbranched propoxylcarbonyl, straight or branched butoxycarbonyl orallyloxycarbonyl; vinyl or substituted vinyl group substitution selectedfrom (C₁ -C₃)alkyl group, halogen, (C₆ -C₁₀)aryl group selected fromphenyl, α-naphthyl, β-naphthyl, substituted (C₆ -C₁₀)aryl group(substitution selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl,nitro, amino, cyano, (C₁ -C₄) alkoxycarbonyl, (C₁ -C₃)alkylamino orcarboxy), halo(C₁ -C₃)alkyl group such as bromomethyl, fluoromethyl,difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl,trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-bromoethyl or 2-iodoethyl, a heterocycle group selected from a fivemembered aromatic or saturated ring with one N, O, S or Se heteroatomoptionally having a benzo or pyrido ring fused thereto: ##STR182##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, or benzothienyl!; (C₁ -C₄)alkoxy group suchas allyloxy, methoxy, ethoxy, n-propoxy, n-butoxy or tert-butoxy; C₆-aryloxy group selected from phenoxy or substituted phenoxy(substitution selected from halo, (C₁ -C₄)alkyl, nitro, cyano, thiol,amino, carboxy, di-(C₁ -C₃)alkylamino); (C₇ -C₁₀)aralkyloxy group suchas benzyloxy, 1-phenylethyloxy or 2-phenylethyloxy; vinyloxy orsubstituted vinyloxy group (substitution selected from (C₁ -C₄)alkyl,cyano, carboxy, or (C₆ -C₁₀)aryl selected from phenyl, α-naphthyl orβ-naphthyl); R^(a) R^(b) amino(C₁ -C₄)alkoxy group, wherein R^(a) R^(b)is a straight or branched (C₁ -C₄)alkyl selected from methyl, ethyl,n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl orR^(a) R^(b) is (CH₂)_(n), n=2-6, or --(CH₂)₂ W(CH₂)₂ -- wherein W isselected from --N(C₁ -C₃)alkyl straight or branched!, --NH, --NOB B isselected from hydrogen or (C₁ -C₃)alkyl!, O or S; or R^(a) R^(b) aminoxygroup, wherein R^(a) R^(b) is a straight or branched (C₁ -C₄)alkylselected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, or 2-methylpropyl or R^(a) R^(b) is (CH₂)_(n), n=2-6, or--(CH₂)₂ W--(CH₂)₂ -- wherein W is selected from --N(C₁ -C₃)alkylstraight or branched!, --NH, --NOB B is selected from hydrogen or (C₁-C₃)alkyl!, O or S;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=1-4,

R⁴ is selected from hydrogen; (C₁ -C₃)alkyl group selected from methyl,ethyl, n-propyl or 1-methylethyl; (C₆ -C₁₀)aryl group selected fromphenyl, α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl group(substitution selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl,nitro, amino, cyano,.(C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino orcarboxy); acyloxy or haloacyloxy group, selected from acetyl, propionyl,chloroacetyl, trichloroacetyl, (C₃ -C₆) cycloalkylcarbonyl, (C₆-C₁₀)aroyl selected from benzoyl or naphthoyl, halo substituted (C₆-C₁₀)aroyl such as pentafluorobenzoyl, 4-chlorobenzoyl, 3-bromobenzoylor 3,4-difluorobenzoyl, (C₁ -C₄)alkylbenzoyl such as 4-toluoyl,2-toluoyl, 4-(1-methylethyl)benzoyl or (heterocycle)carbonyl, theheterocycle selected from a five membered aromatic or saturated ringwith one N, O, S or Se heteroatom optionally having a benzo or pyridoring fused thereto: ##STR183##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR184##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR185## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl, or a six membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl; (C₁ -C₄)alkoxy group such as allyloxy, methoxy,ethoxy, n-propoxy, n-butoxy or tert-butoxy; R^(a) R^(b) amino(C₁-C₄)alkoxy group, wherein R^(a) R^(b) is a straight or branched (C₁-C₄)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, or 2-methylpropyl or R^(a) R^(b) is (CH₂)_(n), n=2-6, or--(CH₂)₂ W(CH₂)₂ -- wherein W is selected from --N(C₁ -C₃)alkyl straightor branched!, --NH, --NOB B is selected from hydrogen or (C₁ -C₃)alkyl!,O or S; or R^(a) R^(b) aminoxy group, wherein R^(a) R^(b) is a straightor branched (C₁ -C₄)alkyl selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R^(a) R^(b)is (CH₂)_(n), n=2-6, or --(CH₂)₂ W--(CH₂)₂ -- wherein W is selected from--N(C₁ -C₃)alkyl straight or branched!, --NH, --NOB B is selected fromhydrogen or (C₁ -C₃)alkyl!, O or S; C₆ -aryloxy group selected fromphenoxy or substituted phenoxy (substitution selected from halo, (C₁-C₄)alkyl, nitro, cyano, thiol, amino, carboxy, di-(C₁ -C₃)alkylamino);(C₁ -C₃)alkylthio group selected from methylthio, ethylthio, propylthioor allylthio; C₆ -arylthio group selected from phenylthio or substitutedphenylthio (substitution selected from halo, (C₁ -C₄)alkyl, nitro,cyano, thiol, amino, carboxy, di-(C₁ -C₃)alkylamino); C₆ -arylsulfonylgroup selected from phenylsulfonyl or substituted phenylsulfonyl(substitution selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl,nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino orcarboxy); a heterocycle group selected from a five membered aromatic orsaturated ring with one N, O, S or Se heteroatom optionally having abenzo or pyrido ring fused thereto: ##STR186##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR187##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR188## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)-alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl, or a six membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl; hydroxy group; α-hydroxy(C₁ -C₃)alkyl groupselected from hydroxymethyl, α-hydroxyethyl, α-hydroxy-1-methylethyl orα-hydroxypropyl; halo(C₁ -C₃)alkyl group such as bromomethyl,fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl,dichloromethyl, trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl,2,2,2-trifluoroethyl, 2-bromoethyl or 2-iodoethyl; acyl or haloacylgroup selected from acetyl, propionyl, chloroacetyl, trifluoroacetyl,(C₃ -C₆)cycloalkylcarbonyl, (C₆ -C₁₀)aroyl selected from benzoyl ornaphthoyl, halo substituted (C₆ -C₁₀)aroyl such as pentafluorobenzoyl,4-chlorobenzoyl, 3-bromobenzoyl or 3,4-difluorobenzoyl, (C₁-C₄)alkylbenzoyl such as 4-toluoyl, 2-toluoyl, or4-(1-methylethyl)benzoyl, or (heterocycle)carbonyl, the heterocycleselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom optionally having a benzo or pyrido ring fusedthereto: ##STR189##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR190##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR191## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl, or a six membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=2-4,

R⁴ is selected from amino; hydroxyamino; straight or branched mono(C₁-C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈).cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl(ethyl)amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.l!hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; (C₆ -C₁₀)arylaminogroup selected from phenylamino or naphthylamino; (C₇-C₁₀)arylalkylamino group selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl orphenylpropylamino; (C₁ -C₄) alkoxycarbonylamino group selected fromtert-butoxycarbonylamino, allyloxycarbonylamino, methoxycarbonylamino,ethoxycarbonylamino or propoxycarbonylamino;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=0,

R^(4') is selected from amino; hydroxyamino; straight or branchedmono(C₁ -C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!-oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl (ethyl) amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino;straight or branched (C₁ -C₃)alkyl group selected from methyl, ethyl,n-propyl or 1-methylethyl; (C₆ -C₁₀)aryl group selected from phenyl,α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl group (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo (C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃) alkylamino or carboxy); aheterocycle group selected from a five membered aromatic or saturatedring with one N, O, S or Se heteroatom optionally having a benzo orpyrido ring fused thereto: ##STR192##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR193##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR194## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl or a six membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxo-thiomorpholinyl;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=1-4,

R^(4') is selected from hydrogen; amino; straight or branched (C₁-C₃)alkyl group selected from methyl, ethyl, n-propyl or 1-methylethyl;(C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl or β-naphthyl;substituted (C₆ -C₁₀)aryl group (substitution selected from halo, (C₁-C₄)alkoxy, trihalo (C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₁ -C₄)alkoxy groupsuch as allyloxy, methoxy, ethoxy, n-propoxy, n-butoxy, iso-butoxy ortert-butoxy; C₆ -aryloxy group selected from phenoxy or substitutedphenoxy (substitution selected from halo, (C₁ -C₄)alkyl, nitro cyano,thiol, amino, carboxy, di-(C₁ -C₃)alkylamino; (C₇ -C₁₀)aralkyloxy groupsuch as benzyloxy, 1-phenylethyloxy or 2-phenylethyloxy; (C₁-C₄)carboxyalkyl group; and the pharmacologically acceptable organic andinorganic salts or metal complexes.

Particularly preferred compounds are compounds according to the aboveformula V and VI in which X is selected from halogen ortrifluoromethanesulfonyloxy; the halogen is selected from bromine,chlorine, fluorine or iodine;

Y is selected from --N₂ ⁺ Cl⁻ or N₃ ;

R or R¹ are selected from nitro; amino; halogen (selected from chlorine,bromine, fluorine or iodine); cyano; hydroxy; or --NR² R³ ;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl or 1,1-dimethylethyl;

and when R² =methyl or ethyl,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or2-methylpropyl;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ is selected from R⁴ (CH₂)_(n) CO-- or R^(4') (CH₂)_(n) SO₂ --;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=0,

R⁴ is selected from hydrogen; amino; hydroxyamino; straight or branchedmono(C₁ -C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl (ethyl) amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl,. 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)arylalkylaminogroup selected from benzyl, 2-phenylethyl, α-phenylethyl,(2-naphthyl)methyl, (1-naphthyl)methyl or phenylpropylamino; straight orbranched (C₁ -C₃)alkyl group selected from methyl, ethyl, n-propyl or1-methylethyl; (C₃ -C₆)cycloalkyl group selected from cyclopropyl,cyclobutyl, cyclopentyl or cyclohexyl; substituted (C₃ -C₆)cycloalkylgroup (substitution selected from (C₁ -C₃)alkyl, cyano, amino or (C₁-C₃)acyl); (C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl orβ-naphthyl; substituted (C₆ -C₁₀)aryl group (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); α-hydroxy(C₁-C₃)alkyl group selected from hydroxymethyl, α-hydroxyethyl,α-hydroxy-1-methylethyl or α-hydroxypropyl; halo(C₁ -C₃)alkyl group suchas bromomethyl, fluoromethyl, difluoromethyl, trifluoromethyl,chloromethyl, dichloromethyl, trichloromethyl, 2-fluoroethyl,2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-bromoethyl or 2-iodoethyl; aheterocycle group selected from a five membered aromatic or saturatedring with one N, O, S or Se heteroatom optionally having a benzo orpyrido ring fused thereto: ##STR195##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR196##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR197## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, I-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl, or a six membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl; acyl or haloacyl group selected from acetyl,propionyl, chloroacetyl, trifluoroacetyl, (C₃ -C₆)cycloalkylcarbonylsuch as cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl,cyclohexylcarbonyl, (2,3-dimethylcyclopropyl)carbonyl,(1,2-dimethylcyclopropyl)carbonyl, (2-ethylcyclopropyl)carbonyl,(2-methylcyclopentyl)carbonyl or (3-ethylcyclobutyl)carbonyl, (C₆-C₁₀)aroyl selected from benzoyl or naphthoyl, halo substituted (C₆-C₁₀)aroyl such as pentafluorobenzoyl, 4-chlorobenzoyl, 3-bromobenzoylor 3,4-difluorobenzoyl, (C₁ -C₄)alkylbenzoyl such as 4-toluoyl,2-methylbenzoyl or 4-(1-methylethyl)benzoyl, or (heterocycle)carbonyl,the heterocycle selected from a five membered aromatic or saturated ringwith one N, O, S or Se heteroatom optionally having a benzo or pyridoring fused thereto: ##STR198##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR199##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR200## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl, pyrazinyl,sym-triazinyl, unsym-triazinyl, pyrimidinyl, or a six membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl; (C₁ -C₄)alkoxycarbonyl group selected frommethoxycarbonyl, ethoxycarbonyl, straight or branched propoxylcarbonyl,straight or branched butoxycarbonyl or allyloxycarbonyl; vinyl orsubstituted vinyl group substitution selected from (C₁ -C₃)alkyl group,halogen, (C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl,β-naphthyl, substituted (C₆ -C₁₀)aryl group (substitution selected fromhalo, (C₁ -C₄)alkoxy, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino orcarboxy), halo(C₁ -C₃)alkyl group such as bromomethyl, fluoromethyl,difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl,trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-bromoethyl or 2-iodoethyl, a heterocycle group selected from a fivemembered aromatic or saturated ring with one N, O, S or Se heteroatomoptionally having a benzo or pyrido ring fused thereto: ##STR201##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, or benzothienyl!; (C₁ -C₄)alkoxy group suchas allyloxy, methoxy, ethoxy, n-propoxy, n-butoxy or tert-butoxy; C₆-aryloxy group selected from phenoxy or substituted phenoxy(substitution selected from halo, (C₁ -C₄)alkyl); (C₇ -C₁ O)aralkyloxygroup such as benzyloxy, 1-phenylethyloxy or 2-phenylethyloxy;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=1-4,

R⁴ is selected from hydrogen; (C₁ -C₃)alkyl group selected from methyl,ethyl, n-propyl or 1-methylethyl; (C₆ -C₁₀)aryl group selected fromphenyl, α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl group(substitution selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl,nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino orcarboxy); acyloxy or haloacyloxy group, selected from acetyl, propionyl,chloroacetyl, trichloroacetyl, (C₃ -C₆) cycloalkylcarbonyl, (C₆-C₁₀)aroyl selected from benzoyl or naphthoyl, halo substituted (C₆-C₁₀)aroyl such as pentafluorobenzoyl, 4-chlorobenzoyl, 3-bromobenzoylor 3,4-difluorobenzoyl, (C₁ -C₄)alkylbenzoyl such as 4-toluoyl,2-toluoyl, 4-(1-methylethyl)benzoyl or (heterocycle)carbonyl, theheterocycle selected from a five membered aromatic or saturated ringwith one N, O, S or Se heteroatom optionaly having a benzo or pyridoring fused thereto: ##STR202##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR203##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR204## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl or pyrazinyl, or a sixmembered saturated ring with one or two N, O, S or Se heteroatoms and anadjacent appended O heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl; (C₁ -C₄)alkoxy group such as allyloxy, methoxy,ethoxy, n-propoxy, n-butoxy or tert-butoxy; C₆ -aryloxy group selectedfrom phenoxy or substituted phenoxy (substitution selected from halo,(C₁ -C₄)alkyl, nitro, cyano, thiol, amino, carboxy, di-(C₁-C₃)alkylamino); (C₁ -C₃)alkylthio group selected from methylthio,ethylthio, propylthio or allylthio; C₆ -arylthio group selected fromphenylthio or substituted phenylthio (substitution selected from halo,(C₁ -C₄)alkyl, nitro, cyano, thiol, amino, carboxy, di-(C₁-C₃)alkylamino); C₆ -arylsulfonyl group selected from phenylsulfonyl orsubstituted phenylsulfonyl (substitution selected from halo, (C₁-C₄)alkoxy, trihalo (C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); a heterocycle groupselected from a five membered aromatic or saturated ring one N, O, S orSe heteroatom optionally having a benzo or pyrido ring fused thereto:##STR205##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR206##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR207## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl or pyrazinyl, or a sixmembered saturated ring with one or two N, O, S or Se heteroatoms and anadjacent appended O heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl; hydroxy group; α-hydroxy(C₁ -C₃)alkyl groupselected from hydroxymethyl, α-hydroxyethyl, α-hydroxy-1-methylethyl orα-hydroxypropyl; halo(C₁ -C₃)alkyl group such as bromomethyl,fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl,dichloromethyl, trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl,2,2,2-trifluoromethyl, 2-bromoethyl or 2-iodoethyl; acyl or haloacylgroup selected from acetyl, propionyl, chloroacetyl, trifluoroacetyl,(C₃ -C₆) cycloalkylcarbonyl, (C₆ -C₁₀)aroyl selected from benzoyl ornaphthoyl, halo substituted (C₆ -C₁₀)aroyl such as pentafluorobenzoyl,4-chlorobenzoyl, 3-bromophenylcarbonyl or 3,4-difluorobenzoyl, (C₁-C₄)alkylbenzoyl such as from 4-toluoyl, 2-toluoyl or4-(1-methylethyl)benzoyl, or (heterocycle)carbonyl, the heterocycleselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom optionally having a benzo or pyrido ring fusedthereto: ##STR208##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl, or benzothienyl, or a five membered aromaticring with two N, O, S or Se heteroatoms optionally having a benzo orpyrido ring fused thereto: ##STR209##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, oxazolyl, benzoxazolyl,indazolyl, thiazolyl or benzothiazolyl, or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom: ##STR210## (A is selected from hydrogen; straight orbranched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)-alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl)

such as γ-butyrolactam, γ-butyrolactone, imidazolidinone orN-aminoimidazolidinone, or a six membered aromatic ring with one tothree N heteroatoms such as pyridyl, pyridazinyl or pyrazinyl, or a sixmembered saturated ring with one or two N, O, S or Se heteroatoms and anadjacent appended O heteroatom such as 2,3-dioxo-1-piperazinyl,4-ethyl-2,3-dioxo-1-piperazinyl, 4-methyl-2,3-dioxo-1-piperazinyl,4-cyclopropyl-2-dioxo-1-piperazinyl, 2-dioxomorpholinyl or2-dioxothiomorpholinyl;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=2-4,

R⁴ is selected from amino; hydroxyamino; straight or branched mono(C₁-C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl (ethyl) amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethyl-cyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers.; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methyl bicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)arylalkylaminogroup selected from benzyl, 2-phenylethyl, α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl) methyl or phenylpropylamino; (C₁-C₄)alkoxycarbonylamino group selected from tert-butoxycarbonylamino,allyloxycarbonylamino, methoxycarbonylamino, ethoxycarbonylamino orpropoxycarbonylamino;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=0,

R^(4') is selected from amino; hydroxyamino; straight or branchedmono(C₁ -C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl (ethyl) amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino;straight or branched (C₁ -C₃)alkyl group selected from methyl, ethyl,n-propyl or 1-methylethyl; (C₆ -C₁₀)aryl group selected from phenyl,α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl group (substitutionselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy); aheterocycle group selected from a five membered aromatic or saturatedring with one N, O, S or Se heteroatom optionally having a benzo orpyrido ring fused thereto: ##STR211##

    Z=N, O, S or Se

such as pyrrolyl, N-methylindolyl, indolyl, 2-pyrrolidinyl,3-pyrrolidinyl, 2-pyrrolinyl, tetrahydrofuranyl, furanyl, benzofuranyl,tetrahydrothienyl, thienyl or benzothienyl;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=1-4,

R^(4') is selected from hydrogen; amino; straight or branched (C₁-C₃)alkyl group selected from methyl, ethyl, n-propyl or 1-methylethyl;and the pharmacologically acceptable organic and inorganic salts ormetal complexes.

Most particularly preferred compounds are compounds according to theabove formula V and VI in which X is selected from halogen ortrifluoromethanesulfonyloxy; the halogen is selected from bromine,chlorine, fluorine or iodine;

Y is selected from --N₂ ⁺ Cl⁻ or N₃ ;

R or R¹ are selected from nitro; amino; halogen (selected from chlorine,bromine, fluorine or iodine); cyano; hydroxy; or --NR² R³ ;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl or 1,1-dimethylethyl;

and when R² =methyl or ethyl,

R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or2-methylpropyl;

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ selected from R⁴ (CH₂)_(n) CO-- or R^(4') (CH₂)_(n) SO₂ --;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=0,

R⁴ is selected from hydrogen; amino; hydroxyamino; straight or branchedmono(C₁ -C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or l-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl(ethyl)amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!-hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁-C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; straight or branched(C₁ -C₂)alkyl group selected from methyl or ethyl; (C₆ -C₁₀)aryl groupselected from phenyl, α-naphthyl or β-naphthyl; substituted (C₆-C₁₀)aryl group (substitution selected from halo, (C₁ -C₄)alkoxy, nitro,amino); α-hydroxy(C₁ -C₃)alkyl group selected from hydroxymethyl;halo(C₁ -C₃)alkyl group such as bromomethyl, fluoromethyl,difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl,trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-bromoethyl or 2-iodoethyl; a heterocycle group selected from a fivemembered aromatic or saturated ring with one N, O, S or Se heteroatomoptionally having a benzo or pyrido ring fused thereto: ##STR212##

    Z=N, O, S or Se

such as indolyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 2-pyrrolinyl,tetrahydrofuranyl, furanyl, benzofuranyl, tetrahydrothienyl or thienyl,or a five membered aromatic ring with two N, O, S or Se heteroatomsoptionally having a benzo or pyrido ring fused thereto: ##STR213##

    Z or Z.sup.1 =N, O, S or Se

such as imidazolyl, pyrazolyl, benzimidazolyl, indazolyl, thiazolyl orbenzothiazolyl; (C₁ -C₄)alkoxycarbonyl group selected frommethoxycarbonyl, ethoxycarbonyl, straight or branched propoxycarbonyl,straight or branched butoxycarbonyl or allyloxycarbonyl; vinyl orsubstituted vinyl group substitution selected from (C₁ -C₃)alkyl group,(C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl, β-naphthyl!; (C₁-C₄)alkoxy group such as allyloxy, methoxy, ethoxy, n-propoxy, n-butoxyor tert-butoxy; C₆ -aryloxy group selected from phenoxy or substitutedphenoxy (substitution selected from halo, (C₁ -C₄)alkyl); (C₇-C₁₀)aralkyloxy group such as benzyloxy, 1-phenylethyloxy or2-phenylethyloxy;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=1-4,

R⁴ is selected from hydrogen; (C₁ -C₂)alkyl group selected from methylor ethyl; (C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl orβ-naphthyl; substituted(C₆ -C₁₀)aryl group (substitution selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl); acyloxy or haloacyloxygroup, selected from acetyl, propionyl, chloroacetyl, trichloroacetyl,(C₃ -C₆)cycloalkylcarbonyl, (C₆ -C₁₀)aroyl selected from benzoyl ornaphthoyl, halo substituted (C₆ -C₁₀)aroyl such as pentafluorobenzoyl,4-chlorobenzoyl, 3-bromobenzoyl or 3,4-difluorobenzoyl, (C₁-C₄)alkylbenzoyl such as 4-toluoyl, 2-toluoyl, 4-(1-methylethyl)benzoylor (heterocycle)carbonyl, the heterocycle selected from a five memberedaromatic or saturated ring with one N, O, S or Se heteroatom optionallyhaving a benzo or pyrido ring fused thereto: ##STR214##

    Z=N, O, S or Se

such as tetrahydrofuranyl, furanyl, benzofuranyl, tetrahydrothienyl,thienyl or benzothienyl, or a five membered aromatic ring with two N, O,S or Se heteroatoms optionally having a benzo or pyrido ring fusedthereto: ##STR215##

    Z or Z.sup.1 =N, O, S or Se

such as pyrazolyl, benzimidazolyl, benzoxazolyl, indazolyl, thiazolyl orbenzothiazolyl, or a six membered aromatic ring with one or two Nheteroatoms such as pyridyl or pyridazinyl; (C₁ -C₄)alkoxy group such asallyloxy, methoxy, ethoxy, n-propoxy, n-butoxy or tert-butoxy;α-hydroxy(C₁ -C₃)alkyl group selected from hydroxymethyl,α-hydroxyethyl, α-hydroxy-1-methylethyl or α-hydroxypropyl; halo(C₁-C₃)alkyl group such as bromomethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-bromoethyl or2-iodoethyl;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=2-4,

R⁴ is selected from amino; hydroxyamino; straight or branched mono(C₁-C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or 1-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; (C₃ -C₈)cycloalkylamino groupselected from cyclopropyl, trans-1,2-dimethylcyclopropyl,cis-1,2-dimethylcyclopropyl, trans-2,3-dimethylcyclopropyl,cis-2,3-dimethylcyclopropyl, cyclobutyl, trans-2,3-dimethylcyclobutyl,cis-2,3-dimethylcyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl, bicyclo 2.2.1!hept-2-yl, or bicyclo 2.2.2!oct-2-ylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched chain di-(C₁ -C₆)alkylamino group selected from dimethylamino,diethylamino, methyl(ethyl)amino, ethyl(1-methylethyl)amino or acombination of methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or1-methyl-1-ethylpropylamino and where appropriate their diastereomersand enantiomers; (C₁ -C₆)alkoxyamino group selected from methoxy,ethoxy, propoxy, butoxy, pentoxy or hexoxyamino; (C₃-C₈)cycloalkoxyamino group selected from cyclopropoxy,trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy,trans-2,3-dimethylcyclopropoxy, cis-2,3-dimethylcyclopropoxy,cyclobutoxy, trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptyloxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, or bicyclo 2.2.1!oct-2-yloxyamino and whereappropriate their diastereomers and enantiomers; (C₇ -C₁₀)aralkoxyaminogroup selected from benzyloxy, 2-phenylethoxy, α-phenylethoxy,(2-naphthyl)methoxy, (1-naphthyl)methoxy, or phenylpropoxyamino; (C₂-C₈)azacycloalkyl group selected from aziridinyl, azetidinyl,pyrrolidinyl, pyrrolinyl, piperidinyl, 2-methylpyrrolidinyl,cis-3,4-dimethylpyrrolidinyl, trans-3,4-dimethylpyrrolidinyl,2-azabicyclo 2.1.1!hex-2-yl, 5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo2.2.1!hept-2-yl, 7-azabicyclo 2.2.1!hept-7-yl, or 2-azabicyclo2.2.2!oct-2-yl and where appropriate their diastereomers andenantiomers; azaheterocycloalkyl group selected from morpholinyl,piperazinyl, 4-methylpiperazinyl, 4-hydroxypiperazinyl, 4-(C₁ -C₄)alkoxypiperazinyl, thiamorpholinyl, tetrahydro-1,2-oxazinyl,isoxazolidinyl, pyrazolidinyl, 2-methylpyrazolidinyl, 2,5-diazabicyclo2.2.2!hept-2-yl, or 2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl and whereappropriate their diastereomers and enantiomers; (C₁-C₄)alkoxycarbonylamino group selected from tert-butoxycarbonylamino,allyloxycarbonylamino, methoxycarbonylamino, ethoxycarbonylamino orpropoxycarbonylamino;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=0,

R^(4') is selected from amino; hydroxyamino; straight or branchedmono(C₁ -C₆)alkylamino group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl or l-methyl-1-ethylpropylamino and where appropriatetheir diastereomers and enantiomers; straight or branched chain di-(C₁-C₆)alkylamino group selected from dimethylamino, diethylamino,methyl(ethyl) amino, ethyl (1-methylethyl)amino or a combination ofmethyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl, 1,1-dimethylethyl, n-pentyl-2-methylbutyl,1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl, n-hexyl,1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl,1,2-dimethylbutyl, 1,3-dimethylbutyl or l-methyl-1-ethylpropylamino andwhere appropriate their diastereomers and enantiomers; straight orbranched (C₁ -C₂)alkyl group selected from methyl or ethyl; (C₆-C₁₀)aryl group selected from phenyl, α-naphthyl or β-naphthyl;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=1-4,

R^(4') is selected from hydrogen; straight or branched (C₁ -C₂)alkylgroup selected from methyl or ethyl; and the pharmacologicallyacceptable organic and inorganic salts or metal complexes.

Compounds of special interest are compound according to the aboveformula in which X is selected from halogen ortrifluoromethanesulfonyloxy; the halogen is selected from bromine,chlorine, fluorine or iodine;

Y is selected from --N₂ ⁺ Cl⁻ or N₃ ;

R or R¹ are selected from nitro; amino; halogen (selected from chlorine,bromine, fluorine or iodine); cyano; hydroxy; or --NR² R³ ;

and when R or R¹ =--NR² R³ and R² =methyl or ethyl;

R³ =methyl or ethyl,

and when R or R¹ =--NR² R³ and R² =hydrogen,

R³ is selected from R⁴ (CH₂)_(n) CO-- or R^(4') (CH₂)_(n) SO₂ --;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=0,

R⁴ is selected from hydrogen; straight or branched (C₁ -C₂)alkyl groupselected from methyl or ethyl; a heterocycle group selected from a fivemembered aromatic or saturated ring with one N, O, or S heteroatomoptionally having a benzo or pyrido ring fused thereto: ##STR216##

    Z=N, O, S or Se

such as furanyl or thienyl, or a five membered aromatic ring with two N,O or S heteroatoms optionally having a benzo or pyrido ring fusedthereto: ##STR217##

    Z or Z.sup.1 =N, O, S or Se

such as pyrazolyl, benzimidazolyl or thiazolyl; (C₁ -C₄)alkoxy groupsuch as allyloxy, methoxy, ethoxy, n-propoxy, n-butoxy or tert-butoxy;C₆ -aryloxy group selected from phenoxy or substituted phenoxy(substitution selected from halo, (C₁ -C₄)alkyl); (C₇ -C₁₀)aralkyloxygroup such as benzyloxy, 1-phenylethyloxy or 2-phenylethyloxy;

and when R³ =R⁴ (CH₂)_(n) CO-- and n=1-4,

R⁴ is selected from hydrogen; (C₁ -C₂)alkyl group selected from methylor ethyl; (C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl orβ-naphthyl;

and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=0,

R^(4') is selected from straight or branched (C₁ -C₂)alkyl groupselected from methyl or ethyl; (C₆ -C₁₀)aryl group selected from phenyl,α-naphthyl or β-naphthyl; and the pharmacologically acceptable organicand inorganic salts or metal complexes.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

The novel compounds of the present invention may be readily prepared inaccordance with the following schemes.

The starting 7-azido-9-(substituted)-6-demethyl-6-deoxytetracyclines or9-azido-7-(substituted)-6-demethyl-6-deoxytetracyclines described informula 1 or the salts thereof are prepared by procedures known to thoseskilled in the art including those described in J. J. Hlavka, et al., J.Am. Chem. Soc., 84, 1426(1962). ##STR218## 1a. R¹ =N₃ and R=NR² R³, R²=R³ 1b. R¹ =N₃ and R=NR² R³, R² ≠R³

1c. R=N₃ and R¹ =NR² R³, R² =R³

1d. R=N₃ and R¹ =NR² R³, R² ≠R³

1e. R¹ =N₃ and R=X, X=halogen, hydrogen

1f. R=N₃ and R¹ =X, X=halogen, hydrogen

The starting 7-azido-9-(substituted)-6-demethyl-6-deoxytetracycline, 1,or 9-azido-7-(substituted)-6-demethyl-6-deoxytetracycline, 1', describedin formula 1 is prepared according to Scheme 1 or Scheme 2. ##STR219##

In accordance with Scheme 1 or 2, a7-amino-9-(substituted)-6-demethyl-6-deoxytetracycline 2, or9-amino-7-(substituted)-6-demethyl-6-deoxytetracycline 2', or theirmineral acid or halide salt, dissolved in 0.1N methanolic hydrogenchloride, is treated with an excess of n-butyl nitrite to give a7-diazonium-9-(substituted)-6-demethyl-6-deoxytetracycline, 3, or9-diazonium-7-(substituted)-6-demethyl-6-deoxytetracycline, 3', or theirmineral acid or halide salt. The formed diazonium compound, 3 or 3', ortheir mineral acid or halide salt, dissolved in 0.1 N methanolichydrogen chloride, is treated with one equivalent of sodium azide togive the corresponding7-azido-9-(substituted)-6-demethyl-6-deoxytetracycline, 1, or9-azido-7-(substituted)-6-demethyl-6-deoxytetracycline, 1', or theirmineral acid or halide salt. ##STR220##

In accordance with Scheme 3 or 4, a7-azido-9-(substituted)-6-demethyl-6-deoxytetracycline, 1, or9-azido-7-(substituted)-6-demethyl-6-deoxytetracycline, 1', or theirmineral acid or halide salt, is treated with a strong acid, such assulfuric acid, hydrochloric acid, methanesulfonic acid,trifluoromethanesulfonic acid, hydrobromic, hydroiodic, or hydrogenfluoride to produce a7-amino-8-(substituted)-9-(substituted)-6-demethyl-6-deoxytetracycline,4, or9-amino-8-(substituted)-7-(substituted)-6-demethyl-6-deoxytetracycline,4', or their mineral acid or halide salt.

The7-amino-8-(substituted)-9-(substituted)-6-demethyl-6-deoxytetracycline,4, or9-amino-8-(substituted)-7-(substituted)-6-demethyl-6-deoxytetracycline,4', or their mineral acid or halide salt, can be further converted asdescribed in Schemes 5, 6, 7 and 8. ##STR221##

In accordance with Scheme 5 or 6, a7-amino-8-(substituted)-9-(substituted)-6-demethyl-6-deoxytetracycline,4, or a9-amino-8-(substituted)-7-(substituted)-6-demethyl-6-deoxytetracycline,4', or their mineral acid or halide salt, is treated with an acylchloride, acyl anhydride, mixed acyl anhydride, sulfonyl chloride orsulfonyl anhydride in the presence of a suitable acid scavenger in avariety of solvents to form the corresponding 7-(acyl or sulfonylamino)-8-(substituted)-9-(substituted)-6-demethyl-6-deoxy-tetracycline,5, or 9-(acyl or sulfonylamino)-8-(substituted)-7-(substituted)-6-demethyl-6-deoxytetracycline,5', or their mineral acid or halide salt. The acid scavenger is selectedfrom sodium bicarbonate, sodium acetate, pyridine, triethylamine,N,O-bis(trimethylsilyl)acetamide,N,O-bis(trimethylsilyl)trifluoroacetamide, potassium carbonate or abasic ion-exchange resin. The solvents are selected from watertetrahydrofuran, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone,hexamethylphosphoramide,1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidinone or1,2-dimethoxyethane. ##STR222##

In accordance with Scheme 7 or 8, a7-amino-8-(substituted)-9-(substituted)-6-demethyl-6-deoxytetracycline,4, or9-amino-8-(substituted)-7-(substituted)-6-demethyl-6-deoxytetracycline,4', or their mineral acid or halide salt, is converted to the respectivediazonium salt, 6 or 6', using procedures known to those skilled in theart including those described in J. J. Hlavka, et al., J. Am. Chem.Soc., 84, 1420(1962).

The diazonium salts, 6 or 6', are reduced to their respective8-(substituted)-7-(substituted)-6-demethyl-6-deoxytetracycline, 7, or8-(substituted)-9-(substituted)-6-demethyl-6-deoxytetracycline, 7', byheating in an alcohol. ##STR223##

In accordance with Scheme 9 or 10, a7-azido-9-(substituted)-6-demethyl-6-deoxytetracycline, 1, or a9-azido-7-(substituted)-6-demethyl-6-deoxytetracycline, 1', is treatedwith trifluoromethanesulfonic acid to give the desired7-amino-9-(substituted)-8-(trifluoromethanylsulfonyloxy)-6-demethyl-6-deoxytetracycline,8, or9-amino-7-(substituted)-8-(trifluoromethanylsulfonyloxy)-6-demethyl-6-deoxytetracycline,8'. ##STR224##

In accordance with Schemes 11-14, Compounds 5, 5', 7, or 7' areselectively N-alkylated in the presence of formaldehyde and either aprimary amine such as methylamine, ethylamine, benzylamine, methylglycinate, (L or D)lysine, (L or D)alanine or their substitutedcongeners; or a secondary amine such as morpholine, pyrrolidine,piperidine or their substituted congeners to give their correspondingMannich base adduct, 9, 9', 10,or 10'.

The7-(substituted)-8-(substituted)-9-(substituted)-6-demethyl-6-deoxytetracyclinesmay be obtained as metal complexes such as aluminum, calcium, iron,magnesium, manganese and complex salts; inorganic and organic salts andcorresponding Mannich base adducts using methods known to those skilledin the art (Richard C. Larock, Comprehensive Organic Transformations,VCH Publishers, 411-415, 1989). Preferably, the7-(substituted)-8-(substituted)-9-(substituted)-6-demethyl-6-deoxytetracyclinesare obtained as inorganic salts such as hydrochloric, hydrobromic,hydroiodic, phosphoric, nitric or sulfate; or organic salts such asacetate, benzoate, citrate, cysteine or other amino acids, fumarate,glycolate, maleate, succinate, tartrate, alkylsulfonate or arysulfonate.In all cases the salt formation occurs with the C(4)-dimethylaminogroup. The salts are preferred for oral and parenteral administration.

BIOLOGICAL ACTIVITY

Method for in Vitro Antibacterial Evaluation

(Table I)

The minimum inhibitory concentration (MIC), the lowest concentration ofthe antibiotic which inhibits growth of the test organism, is determinedby the agar dilution method using Muller-Hinton II agar (BaltimoreBiological Laboratories). An inoculum density of 1-5×10⁵ CFU/ml and anantibiotic concentration (32-≦0.015 μg/ml) is used. The plates areincubated for 18 hours at 35° C. in a forced air incubator. The testorganisms comprise strains sensitive to tetracycline and geneticallydefined strains that are resistant to tetracycline, due to inability tobind bacterial ribosomes (tetM).

E. coli in Vitro Protein Translation System (Table II)

An in vitro, cell free, protein translation system using extracts fromE. coli strain MRE 600 (tetracycline sensitive) and a derivative of MRE600 containing the tetM determinant has been developed based onliterature methods J. M. Pratt, Coupled Transcription-translation inProkaryotic Cell-free Systems, Transcription and Translation, aPractical Approach, (B. D. Hames and S. J. Higgins, eds) p. 179-209, IRLPress, Oxford-Washington, 1984!.

Using the system described above, the tetracycline compounds of thepresent invention are tested for their ability to inhibit proteinsynthesis in vitro. Briefly, each 10 μl reaction contains S30 extract (awhole extract) made from either tetracycline sensitive cells or anisogenic tetracycline resistant (tetM) strain, low molecular weightcomponents necessary for transcription and translation (i.e., ATP andGTP), a mix of 19 amino acids (no methionine), ³⁵ S labeled methionine,DNA template (either pBR322 or pUC119), and either DMSO (control) or thenovel tetracycline compound to be tested ("novel TC") dissolved in DMSO.

The reactions are incubated for 30 minutes at 37° C. Timing is initiatedwith the addition of the S30 extract, the last component to be added.After 30 minutes, 2.5 μl of the reaction is removed and mixed with 0.5ml of 1N NaOH to destroy RNA and tRNA. Two to three ml of 25%trichloroacetic acid is added and the mixture incubated at roomtemperature for 15 minutes. The trichloroacetic acid precipitatedmaterial is collected on Whatman GF/C filters and washed with a solutionof 10% trichloroacetic acid. The filters are dried and the retainedradioactivity, representing incorporation of ³⁵ S-methionine intopolypeptides, is counted using standard liquid scintillation methods.

The percent inhibition (P.I.) of protein synthesis is determined to be:##EQU1## In Vivo Antibacterial Evaluation (Table III)

The therapeutic effects of tetracyclines are determined against an acutelethal infection with Staphylococcus aureus strain Smith (tetracyclinesensitive). Female, mice, strain CD-1 (Charles River Laboratories), 20±2grams, are challenged by an intraperitoneal injection of sufficientbacteria (suspended in hog mucin) to kill non-treated controls within24-48 hours. Antibacterial agents, contained in 0.5 ml of 0.2% aqueousagar, are administered subcutaneously or orally 30 minutes afterinfection. When an oral dosing schedule is used, animals are deprived offood for 5 hours before and 2 hours after infection. Five mice aretreated at each dose level. The 7 day survival ratios from 3 separatetests are pooled for calculation of median effective dose (ED₅₀).

Testing Results

The claimed compounds exhibit antibacterial activity against a spectrumof tetracycline sensitive and resistant Gram-positive and Gram-negativebacteria, especially, strains of E. coli, S. aureus and E. faecalis,containing the tetM resistance determinants (Table I). Notable is8-chloro-9-(formylamino)-4-(dimethylamino)-6-demethyl-6-deoxytetracycline,compound A in Table I, which has good in vitro activity againsttetracycline resistant strains containing the tetM resistancedeterminant (such as S. aureus UBMS 88-5 and S. aureus UBMS 90-1 and90-2) and is equally as effective as minocycline against tetracyclinesusceptible strains.

Protein synthesis, determined using cell-free extracts from thetetracycline susceptible strain MRE600, is inhibited by tetracycline,minocycline and the8-chloro-9-(formylamino)-4-(dimethylamino)-6-demethyl-6-deoxytetracyclineof this invention (Table II). Protein synthesis, determined usingcell-free extracts from strain MRE600 (tetM), is resistant totetracycline and minocycline, since less than 20% inhibition is achievedeven at 1 mg/ml concentration of minocycline vs 90% inhibition at0.3mg/ml of the tetracycline sensitive ribosome extracts prepared fromstrain MRE600 (Table II). In contrast,8-chloro-9-(formylamino)-4-(dimethylamino)-6-demethyl-6-deoxytetracyclineeffectively inhibited protein synthesis in extracts prepared from eitherMRE600 or MRE600 (tetM) (Table II). The evidence presented indicatesthat8-chloro-9-(formylamino)-4-(dimethylamino)-6-demethyl-6-deoxytetracyclineis an inhibitor of protein synthesis at the ribosome level. The abilityof8-chloro-9-(formylamino)-4-(dimethylamino)-6-demethyl-6-deoxytetracyclineto inhibit bacterial growth almost certainly reflects directedinhibition of bacterial protein synthesis. Therefore, it is expected toexhibit a bacteriostatic effect against susceptible bacteria, as is thecase with other tetracyclines.

The antibacterial activity of8-chloro-9-(formylamino)-4-(dimethylamino)-6-demethyl-6-deoxytetracyclineis also demonstrated by in vivo efficacy in animals infected with S.aureus Smith (Table III).

The improved efficacy of8-chloro-9-(formylamino)-4-(dimethylamino)-6-demethyl-6-deoxytetracyclineis demonstrated by the in vitro activity against isogenic strains intowhich the resistance determinants, such as tetM, were cloned (Table I);the inhibition of protein synthesis by tetM ribosomes (Table II); andthe in vivo activity against experimental infections (Table III).

    ______________________________________    LEGEND FOR COMPOUNDS    LETTER      NAME    ______________________________________    A           8-Chloro-4-(dimethylamino)-9-(formyl-                amino)-1,4,4a,5,5a,6,11,12a-octahydro-                3,10,12,12a-tetrahydroxy-1,11-dioxo-2-                naphthacenecarboxamide hydrochloride or                sulfate    B           8-Chloro-4,7-bis(dimethylamino)-1,4,4a,5-                5a,6,11,12a-octahydro-3,10,12,12a-tetra-                hydroxy-1,11-dioxo-2-naphthacenecarbox-                amide sulfate    C           7-Amino-8-chloro-4-(dimethylamino)-1,4-                4a,5,5a,6,11,12a-octahydro-3,10,12,12a-                tetrahydroxy-1,11-dioxo-2-naphthacene-                carboxamide hydrochloride    D           8-(Aminocarbonyl)-2-chloro-10-(dimethyl-                amino)-5,6a,10,10a,11,11a,12-octahydro-                5,7-dioxo-1-naphthacenediazonium                chloride    E           8-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6-                11,12a-octahydro-3,10,12,12a-tetrahydroxy-                1,11-dioxo-2-naphthacenecarboxamide                sulfate    F           8-Chloro-4,7-bis(dimethylamino)-9-                (formylamino)-1,4,4a,5,5a,6,11,12a-octa-                hydro-3,10,12,12a-tetrahydroxy-1,11-di-                oxo-2-naphthacenecarboxamide sulfate    G           9-Amino-8-chloro-4-(dimethylamino)-1,4,-                4a,5,5a,6,11,12a-octahydro-3,10,12,12a-                tetrahydroxy-1,11-dioxo-2-naphthacenecar-                boxamide    H           9-Amino-8-chloro-4,7-(dimethylamino)-1,4-                4a,5,5a,6,11,12a-octahydro-3,10,12,12a-                tetrahydroxy-1,11-dioxo-2-naphthacenecar-                boxamide sulfate    I            7S-(7alpha, 10aalpha)!- 9-(Aminocarbo-                nyl)-3-chloro-7-(dimethylamino)-5,5a,6-                6a,7,10,10a,12-octahydro-1,8,10a,11-                tetrahydroxy-10,12-dioxo-2-naphthacenyl!-                carbamic acid methyl ester    J            4S-(4alpha, 12aalpha)!-8-Chloro-4-(di-                methylamino)-9-hydrazino-1,4,4a,5,5a,6-                11,12a-octahydro-3,10,12,12a-tetra-                hydroxy-1,11-dioxo-2-naphthacenecarbox-                amide monohydrochloride    K           Tetracycline hydrochloride    L           Minocycline hydrochloride    M            4S(4alpha,12aalpha)!-9-Amino-8-chloro-7-                (diethylamino)-4-dimethylamino)-1,4,4a,-                5,5a,6,11,12a-octahydro-3,10,12,12a-                tetrahydroxy-1,11-dioxo-2-naphthacene-                carboxamide    ______________________________________

                                      TABLE I    __________________________________________________________________________    ANTIBACTERIAL ACTIVITY OF 8-(HALOGEN)-7-(SUBSTITUTED)-9-(SUBSTITUTED)-6-DE    METHYL-6-DEOXYTETRACYCLINES    MIC (ug/ml)               Compound    Organism   A   B   C   D    E   F    G   H    I   J    K   L    __________________________________________________________________________    E. coli UBMS 88-1               32  >32 >32 >32  >32 >32  >32 >32  =32 32   >32 16    (tetB)    E. coli UBMS 88-2               0.12                   8   2   32   16  1    4   8    NT  2    0.25                                                               0.25    (sensitive)    E. coli UBMS 89-1               NG  >32 32  32   16  0.5  NG  NG   8   16   16  8    (tetM)    E. coli UBMS 89-2               0.25                   16  4   32   16  1    4   16   16  4    1   1    (sensitive)    E. coli ATCC 25922               0.12                   8   2   16   8   0.25 1   4    8   1    0.5 0.5    S. aureus UBMS 88-4               <0.015                   0.03                       0.5 0.5  0.25                                    0.12 <0.015                                             0.12 0.06                                                      0.06 0.12                                                               0.03    (sensitive)    S. aureus UBMS 88-5               0.12                   0.5 32  4    2   0.25 1   1    0.5 0.5  >32 4    (tetM)    S. aureus UBMS 88-7               16  0.5 >32 8    4   4    2   0.25 2   1    >32 0.12    (tetK)    S. aureus UBMS 90-1               0.25                   0.05                       32  4    2   0.5  1   2    0.5 0.5  >32 4    (tetM)    S. aureus UBMS 90-3               <0.015                   0.06                       0.12                           0.5  0.12                                    0.06 <0.015                                             0.12 0.06                                                      0.03 0.06                                                               0.03    (sensitive)    S. aureus UBMS 90-2               0.03                   0.5 8   2    1   0.12 0.25                                             0.5  0.5 0.5  32  4    (tetM)    S. aureus IVES 2943               32  1   >32 16   4   8    8   1    4   2    >32 4    (meth. resistant)    S. aureus SMITH (MP)               <0.015                   0.06                       0.25                           0.5  0.12                                    0.06 <0.015                                             0.06 0.06                                                      0.03 0.06                                                               0.03    (sensitive)    S. aureus IVES 1983               32  1   >32 16   4   8    8   4    4   2    >32 4    (MP) (meth. resistant)    S. aureus ATCC 29213               <0.015                   ≦0.015                       0.12                           0.12 0.03                                    0.06 <0.015                                              0.015                                                  ≦0.015                                                      ≦0.015                                                           ≦0.015                                                               ≦0.015    (sensitive)    Enteroc. spp. 12201               0.5 1   32  2    1   0.5  2   4    2   0.05 32  8    S. faecal. ATCC 29212               <0.015                   1   8   2    2   0.06 0.25                                             0.5  0.5 0.5  16  1    S. haemol. AVAH 88-3               NT  0.25                       1   1    0.5 0.12 0.12                                             0.12 0.5 0.25 1   0.12    __________________________________________________________________________     NG = No growth     NT = Not tested

                  TABLE II    ______________________________________    INHIBITION OF PROTEIN SYNTHESIS BY E. COLI    CELL-FREE RIBOSOMES WITH TETRACYCLINES                    % Inhibition    Compound  Conc.       Wild Type S30                                     tetM S30    ______________________________________    H              1.0   mg/ml  57       29                   0.3   mg/ml  62       21                   0.1   mg/ml  52       19    L              1.0   mg/ml  90       19                   0.3   mg/ml  91        0                   0.1   mg/ml  66        0    A              1.0   ml/ml  93       NT                   0.3   mg/ml  98       NT    ______________________________________     NT = Not Tested

                  TABLE III    ______________________________________    PROTECTIVE ACTIVITY IN MICE INFECTED WITH    STAPHYLOCOCCUS AUREUS SMITH    Compound      ED.sub.50 (mg/kg)    ______________________________________    H                 4-8    B                 >16    M                 >16    A         HCL     4-8    A         H.sub.2 SO.sub.4                      4-8    J                 >16    ______________________________________

When the compounds are employed as antibacterials, they can be combinedwith one or more pharmaceutically acceptable carriers, for example,solvents, diluents and the like, and may be administered orally in suchforms as tablets, capsules, dispersible powders, granules, orsuspensions containing, for example, from about 0.05 to 5% of suspendingagent, syrups containing, for example, from about 10 to 50% of sugar,and elixirs containing, for example, from about 20 to 50% ethanol, andthe like, or parenterally in the form of sterile injectable solutions orsuspensions containing from about 0.05 to 5% suspending agent in anisotonic medium. Such pharmaceutical preparations may contain, forexample, from about 25 to about 90% of the active ingredient incombination with the carrier, more usually between about 5% and 60% byweight.

An effective amount of compound from 2.0 mg/kg of body weight to 100.0mg/kg of body weight should be administered one to five times per dayvia any typical route of administration including but not limited tooral, parenteral (including subcutaneous, intravenous, intramuscular,intrasternal injection or infusion techniques), topical or rectal, indosage unit formulations containing conventional non-toxicpharmaceutically acceptable carriers, adjuvants and vehicles. It will beunderstood, however, that the specific dose level and frequency ofdosage for any particular patient may be varied and will depend upon avariety of factors including the activity of the specific compoundemployed, the metabolic stability and length of action of that compound,the age, body weight, general health, sex, diet, mode and time ofadministration, rate of excretion, drug combination, the severity of theparticular condition, and the host undergoing therapy.

These active compounds may be administered orally as well as byintravenous, intramuscular, or subcutaneous routes. Solid carriersinclude starch, lactose, dicalcium phosphate, microcrystallinecellulose, sucrose and kaolin, while liquid carriers include sterilewater, polyethylene glycols, non-ionic surfactants and edible oils suchas corn, peanut and sesame oils, as are appropriate to the nature of theactive ingredient and the particular form of administration desired.Adjuvants customarily employed in the preparation of pharmaceuticalcompositions may be advantageously included, such as flavoring agents,coloring agents, preserving agents, and antioxidants, for example,vitamin E, ascorbic acid, BHT and BHA.

The preferred pharmaceutical compositions from the standpoint of ease ofpreparation and administration are solid compositions, particularlytablets and hard-filled or liquid-filled capsules. Oral administrationof the compounds is preferred.

These active compounds may also be administered parenterally orintraperitoneally. Solutions or suspensions of these active compounds asa free base or pharmacologically acceptable salt can be prepared inwater suitably mixed with a surfactant such as hydroxypropylcellulose.Dispersions can also be prepared in glycerol, liquid, polyethyleneglycols and mixtures thereof in oils. Under ordinary conditions ofstorage and use, these preparations contain a preservative to preventthe growth of microorganisms.

The pharmaceutical forms suitable for injectable use include sterileaqueous solutions or dispersions and sterile powders for theextemporaneous preparation of sterile injectable solutions ordispersions. In all cases, the form must be sterile and fluid. It mustbe stable under the conditions of manufacture and storage and must bepreserved against the contaminating action of microorganisms such asbacteria and fungi. The carrier can be a solvent or dispersion mediumcontaining, for example, water, ethanol, polyol (e.g., glycerol,propylene glycol and liquid polyethylene glycol), suitable mixturesthereof, and vegetable oil.

The invention will be more fully described in 5 conjunction with thefollowing specific examples which are not to be construed as limitingthe scope of the invention.

EXAMPLE 1 7S-(7alpha,10alpha)!9-(Aminocarbonyl)-4,7-bis(dimethylamino)-5,5a,6,6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthacenediazonium Chloride Sulfate(1:1)

To a 0° C. solution of 3.0 g of9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,-10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamidesulfate dissolved in 100 ml of 0.1N methanolic hydrogen chloride isadded, dropwise, 6.6 ml of butyl nitrite. The reaction is stirred at 0°C. for 1 hour, poured into 400 ml of diethyl ether, collected and driedto give 2.64 g of the desired product.

MS(FAB): m/z 484 (M+H)

EXAMPLE 2 4S-(4alpha,12aalpha)!9-Azido-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11,dioxo-2-naphthacenecarboxamideHydrochloride (1:1)

To a room temperature solution of 2.64 g of product from Example 1dissolved in 84 ml of 0.1N methanolic hydrogen chloride is added 0.353 gof sodium azide. The mixture is stirred at room temperature for 4 hours,poured into 500 ml of diethyl ether and collected to give 2.5 g of thedesired product.

IR(KBr): 2080 cm⁻¹.

EXAMPLE 3 4S-(4α,12aα)!-9-Amino-8-chloro-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2Naphthacenecarboxamide Sulfate

One gram of product from Example 2 is added to 10 ml of 0° C.concentrated sulfuric acid. The reaction is stirred at 0° C. for 1.5hours, poured into 500 ml of diethyl ether, collected and dried to give1.1 g of the desired product.

MS(FAB): m/z 507 (M+H).

EXAMPLE 44S-(4α,12aα)!-8-Chloro-4,7-bis(dimethylamino)-9-(formylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamideSulfate (1:1)

To a 0 ° C. solution of 0.092 g of product from Example 3 dissolved in5.0 ml of 98% formic acid is added 0.0164 g of sodium acetate. Theresulting mixture is stirred at 0° C. for 10 minutes, followed by theaddition of 0.23 ml of acetic anhydride. The reaction is stirred at roomtemperature of 1 hour, poured into diethyl ether and collected to give0.045 g of solid. The collected solid is triturated with 50 ml of ethylacetate and filtered. The filtrate is concentrated in vacuo to give0.019 g of the desired product.

MS(FAB): m/z 535 (M+H).

EXAMPLE 5 4S-(4α,12aα)!-8-Chloro-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamideSulfate (1:1)

To a 0° C. solution of 0.090 g of product from Example 3 dissolved in 35ml of 0.1N methanolic hydrogen chloride is added 0.2 ml of butylnitrite. The reaction is stirred at room temperature for 1 hour, pouredinto 70 ml of diethyl ether and collected give 0.070 g of the desireddiazonium chloride intermediate.

A solution of 0.070 g of the above intermediate dissolved in 20 ml ofmethyl alcohol is heated at the reflux temperature for 45 minutes,poured into diethyl ether and collected to give 0.056 g of the desiredproduct.

MS(FAB): m/z 491 (M⁺).

EXAMPLE 64S-(4α,12aα)!-7-Amino-8-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamideHydrochloride (1:1)

Three grams of 7-azido-6-demethyl-6-deoxytetracycline hydrochloride,prepared by the procedure described in J. Am. Chem. Soc., 84:1426-1430,is added to 120 ml of cold concentrated hydrochloric acid and stirredfor 13/4 hours at ice bath temperature. The reaction mixture isconcentrated in vacuo to give 2.9 g of the desired product.

MS(FAB): m/z 464 (M+H).

EXAMPLE 76aS-(6aα,10aα)!-8-(Aminocarbonyl)-2-chloro-10-(dimethylamino)-5,6a,10,10a,11,11a,12-octahydro-5,7-dioxo-1-naphthaCenediazonium Chloride Hydrochloride

To a 0° C. solution of 0.50 g of product from Example 6 dissolved in 15ml of 0.1N methanolic hydrogen chloride is added 1.0 ml of butylnitrite. The reaction is stirred at 0° C. for 1 hour, poured into 500 mlof diethyl ether and collected to give 0.48 g of the desired product.

IR(KBr): 2200 cm⁻¹.

EXAMPLE 8 4S-(4alpha,12aalpha)!7-Azido-8-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12atetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide Hydrochloride

To a room temperature solution of 0.48 g of product from Example 7dissolved in 20 ml of 0.1N methanolic hydrogen chloride is added 0.055 gof sodium azide. The reaction mixture is stirred at room temperature for4 hours, poured into 100 ml of diethyl ether and collected to give 0.366g of the desired product.

MS(FAB): m/z 490 (M+H).

EXAMPLE 94s-(4α,12aα)!-8-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamideHydrochloride (1:1)

To a 0° C. solution of 0.095 g of product from Example 6 dissolved in 5ml of 0.1N methanolic hydrogen chloride is added 0.3 ml of butylnitrite. The reaction mixture is stirred at 0° C. for 1 hour, pouredinto diethyl ether and collected to give 0.070 g of the desiredintermediate.

A solution of 0.050 g of the above intermediate dissolved in 15 ml ofmethyl alcohol is heated at the reflux temperature for 1 hour andconcentrated in vacuo to give 0.035 g of the desired product.

MS(FAB): m/z 449 (M+H).

EXAMPLE 104S-(4α,12aα)!-9-Amino-8-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamideHydrochloride (1:1)

To 10 ml of concentrated hydrochloric acid at 0° C. is added 0.20 g of9-azido-6-demethyl-6-deoxytetracycline hydrochloride prepared by theprocedure described in J. Am. Chem. Soc., 84: 1426-1430. The reaction isstirred at 0 C for 1 1/2 hours and concentrated in vacuo to give 0.195 gof the desired product.

MS(FAB): m/z 464 (M+H).

EXAMPLE 11 4S-(4α,12aα)!-8-Chloro-4-(dimethylamino)-9-(formylamino)-1,44a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamideHydrochloride (1:1)

To a 0° C. solution of 0.103 g of product from Example 10, as thehydrochloride, dissolved in 6 ml of 98% formic acid is added 0.23 ml ofacetic anhydride. The resulting mixture is stirred 0° C. for 5 minutesfollowed by 1 hour at room temperature. The reaction is poured into 500ml of diethyl ether and collected to give 0.090 g of the desiredproduct.

MS(FAB): m/z 492 (M+H).

EXAMPLE 124S-(4α,12aα)!-7-Amino-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-iodo-1,11-dioxo-2-naphthacenecarboxamideSulfate (1:1)

To a 0° C. solution of 0.285 g of 7-amino-6-demethyl-6-deoxytetracyclinedissolved in 5 ml of concentrated sulfuric acid is added 1.2 equivalentsof N-iodosuccinimide. The reaction is stirred at 0° C. for 15 minutesthen poured into 400 ml of diethyl ether. The resulting solid iscollected and dried to give 0.23 g of the desired product.

¹ H NMR(DMSO-d₆): Δ8.0 (C-8H).

EXAMPLE 13 6aS-(6aalpha,10aalpha)!8-(Aminocarbonyl)-10-(dimethylamino)-5,6a,7,10,10a,11,11a,12-octahydro-4,6,6a,9-tetrahydroxy-3-iodo-5,7-dioxo-1-naphthacenediazoniumChloride Sulfate (1:1:1)

To a 0° C. solution of 0.15 g of product from Example 12 dissolved insufficient 0.1N methanolic hydrogen chloride to affect solution isadded, dropwise, 0.143 ml of n-butyl nitrite. The reaction is stirred at0° C. for 30-45 minutes then poured into cold, stirring diethyl ether.The resulting solid is collected, washed with diethyl ether and dried togive 0.12 g of the desired product.

¹ H NMR(DMSO-d₆):Δ8.52 (C-8H).

EXAMPLE 14 4S-(4alpha,12aalpha)!7-Azido-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-iodo-1,11-dioxo-2-naphthacenecarboxamideSulfate (1:1)

The title compound is prepared by the procedure of Example 8, using 2.2g of product from Example 13, 60 ml of 0.1N methanolic hydrogen chlorideand 0.203 g of sodium azide to give (after purification) 0.65 g of thedesired product.

IR(KBr): 2100 cm⁻¹.

MS(FAB): m/z 582 (M+H).

EXAMPLE 15 4S-(4alpha,12aalpha)!7-Amino-8-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-iodo-1,11-dioxo-2-naphthacenecarboxamideSulfate (1:1)

A mixture of 0.2 g of product from Example 14 and 1 ml of concentratedhydrochloric acid is stirred at room temperature for 2 hours. Thereaction mixture is triturated with iso-propanol and ether, collectedand dried to give 0.18 g of the desired product.

MS(FAB): m/z 590 (M+H).

EXAMPLE 16 7S-(7alpha,10aalpha)!9-(Aminocarbonyl)-4-(diethylamino)-7-(dimethylamino)-5,5a,6,6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthacenediazoniumChloride Sulfate (2:1)

To a 0° C. solution of 1.85 g9-amino-7-(diethylamino)-6-demethyl-6-deoxytetracycline, prepared by theprocedure described in U.S. patent application Ser. No. 07/771,697,filed Oct. 4, 1991 dissolved in 40 ml of 0.1N methanolic hydrogenchloride is added 1.85 ml of n-butyl nitrite. The reaction mixture isstirred at 0° C for 2 hours, poured into diethyl ether, the solid iscollected and washed with diethyl ether to give 2.1 g of the desiredproduct.

¹ H NMR(DMSO-d₆): δ7.9 (C-8H).

EXAMPLE 17 4S-(4alpha,12aalpha)!9-Azido-7-(diethylamino)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamideDisulfate

To a room temperature solution of 1.192 g of product from Example 16dissolved in 75 ml of 0.1N methanolic hydrogen chloride is added 0.104 gof sodium azide. The reaction is stirred at room temperature for 2hours, poured slowly into diethyl ether and collected to give 0.8 g ofthe desired product.

¹ H NMR(DMSO-d₆): δ7.5 (C-8H).

EXAMPLE 18 4S-(4alpha,12aalpha)!9-Azido-7-(diethylamino)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamideDihydrochloride

To a room temperature solution of 0.6 g of product from Example 17dissolved in water is added solid sodium acetate to achieve pH 5. Themixture is extracted 2 times with chloroform, the organic layer is driedover sodium sulfate and concentrated in vacuo. The residue isredissolved in 5 ml of methanol and 2 drops of concentrated hydrochloricacid is added. The reaction solution is then added dropwise to 120 ml ofdiethyl ether. The resulting solid is collected to give 0.4 g of thedesired product.

IR(KBr): 2100 cm⁻¹.

EXAMPLE 19 4S-(4alpha,12aalpha)!9-Amino-8-chloro-7-(diethylamino)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamideSulfate

A mixture of 0.23 g of product from Example 18 and 5 ml of concentratedhydrochloric acid is stirred at room temperature for 2 hours. Theresulting solid is triturated with isopropanol and diethyl ether. Thesolid is collected, washed with diethyl ether and dried to give 0.21 gof the desired product.

MS(FAB): m/z 535 (M+H).

EXAMPLE 20 7S-(7alpha, 10aalpha)!9-(Aminocarbonyl)-3-chloro-7-(dimethylamino)-5,5a,6,6a,7,10,10a,12-octahydro-8,-10a,11-tetrahydroxy-10,12-dioxo-2-naphthacenyl!carbamicAcid Methyl Ester

To a room temperature solution of 0.20 g of product from Example 10,dissolved in 4 ml of 1-methyl-2-pyrrolidinone, is added 0.30 g of sodiumbicarbonate. The mixture is stirred for 5 minutes followed by theaddition of 34 μl of methyl chloroformate. The reaction is stirred atroom temperature for 1 hour, filtered into 200 ml of diethyl ether andcollected to give 0.066 g of the desired product.

MS(FAB): m/z 522 (M+H).

EXAMPLE 21 4S-(4alpha,12aalpha)!8-Chloro-4-(dimethylamino)-9-hydrazino-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamideMonohydrochloride

To 0.30 g of product from Example 10, dissolved in 8 ml of 0.10Nmethanolic hydrogen chloride, is added 0.60 ml of n-butyl nitrite. Thereaction is stirred at ice bath temperature for 1 hour, poured into 200ml of diethyl ether and collected to give 0.260 g. Fifty milligrams ofthe collected material is added to 3 ml of 6% sulfurous acid, stirred atroom temperature for 1 hour and concentrated in vacuo to give 0.037 g ofthe desired product.

CI-MS: m/z 479 (M+H).

EXAMPLE 22 4S-(4alpha,12aalpha)!9-Amino-4,7-bis(dimethylamino)-8-fluoro-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamideHydrochloride

The title compound is prepared by the procedure of Example 3, using theproduct from Example 2 and liquid hydrogen fluoride.

EXAMPLE 23 6aS-(6aalpha,10alpha)!3-Amino-8-(aminocarbonyl)-10-(dimethylamino)-5,6a,7,10,10a,11,11a,12-octahydro-4,66a,9-tetrahydroxy-5,7-dioxo-2-naphthacenyl EsterTrifluoromethanesulfonic Acid

The title compound is prepared by the procedure of Example 3, using9-azido-6-demethyl-6-deoxytetracycline prepared by the proceduredescribed in J. Am. Chem. Soc., 84:1426-1430 andtrifluoromethanesulfonic acid.

EXAMPLE 24 4S-(4alpha,12aalpha)!9-Amino-4-(dimethylamino)-8-fluoro-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamideHydrochloride

The title compound is prepared by the procedure of Example 22, using9-azido-6-demethyl-6-deoxytetracycline prepared by the proceduredescribed in the above reference.

EXAMPLE 25 4S-(4alpha,12aalpha)!4-(Dimethylamino)-8-fluoro-9-(formylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12-12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamideHydrochloride

The title compound is prepared by the procedure of Example 4, using theproduct from Example 24.

EXAMPLE 26 4S-(4alpha,12aalpha)!4-(Dimethylamino)-8-fluoro-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide Hydrochloride

The title compound is prepared by the procedures described in Examples 1and 5, using the product from Example 24.

EXAMPLE 27 4S-(4alpha,12alpha)!4.7-Bis(dimethylamino)-8-fluoro-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide

The title compound is prepared by the procedure of Example 5, using theproduct of Example 22.

EXAMPLE 28 7S-(7alpha, 10aalpha)!9-(Aminocarbonyl)-7-(dimethylamino)-3-fluoro-5,5a,6,6a,7,10,10a,12-octahydro-1,8-10a,11-tetrahydroxy-10,12-dioxo-2-naphthacenyl!carbamicAcid Methyl Ester

The title compound is prepared by the procedure of Example 20, using theproduct from Example 24.

EXAMPLE 29 6aS-(6aalpha,10alpha)!3-Amino-8-(aminocarbonyl)-1,10-bis(dimethylamino)-5,6a,7,10,10a,11,11a,12-octahydro-4,6,6a,9-tetrahydroxy-5,7-dioxo-2-naphthacenylEster Trifluoromethanesulfonic Acid

The title compound is prepared by the procedure of Example 3, using theproduct from Example 3 and trifluoromethanesulfonic acid.

EXAMPLE 30 4S-(4alpha,12aalpha)!7-Amino-4-(dimethylamino)-8-fluoro-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamideHydrochloride

The title compound is prepared by the procedure of Example 3, using7-azido-6-demethyl-6-deoxytetracycline prepared by the proceduredescribed in J. Am. Chem. Soc., 84:1426-1430 and liquid hydrogenfluoride at -30° C.

EXAMPLE 31 7S-(7alpha, 10aalpha)!9-(Aminocarbonyl)-3-chloro-4,7-bis(dimethylamino)-5,5a,6,6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthacenyl!carbamicAcid 2-(dimethylamino)ethyl Ester

The title compound is prepared by the procedure of Example 27, using theproduct from the Example 3 and beta-dimethylaminoethyl chloroformate.

EXAMPLE 32 4S-(4alpha,12aalpha)!8-Chloro-9-(diethylamino)-oxy!carbonyl!amino!4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11dioxo-2-naphthacenecarboxamide

The title compound is prepared by the procedure of Example 27, using theproduct from Example 3 and diethylaminoxy chloroformate.

EXAMPLE 334S-(4alpha,12aalpha)!8-Chloro-7-(diethylamino)-4-(dimethylamino)-9-(formylamino)-1,4,4a,5,5a,6,11,-12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamideSulfate

The title compound is prepared by the procedure of Example 4, using theproduct from Example 19.

EXAMPLE 34 6aS-(6aalpha,10alpha)!8-(Aminocarbonyl)-2-chloro-10-(dimethylamino)-5,6a,7,10,10a,11,11a,12-octahydro-4,6,6a,9-tetrahydroxy-5,7-dioxo-1-naphthacenyl!-carbamicAcid Methyl Ester

The title compound is prepared by the procedure of Example 20, using theproduct from Example 6.

EXAMPLE 354S-(4α,12aα)!-4-(Dimethylamino)-8-fluoro-7-(formylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamideHydrochloride

The title compound is prepared by the procedure of Example 4, using theproduct from Example 8.

EXAMPLE 36 7S-(7alpha,10aalpha)!9-(Aminocarbonyl)-7-(dimethylamino)-3-fluoro-5,5a,6,6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthacenyl!-carbamicAcid Methyl Ester

The title compound is prepared by the procedure of Example 20, using theproduct from Example 24.

EXAMPLE 377S-(7alpha,10aalpha)!9-(Aminocarbonyl)-7-(dimethylamino)-3-fluoro-5,5a,6,6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-carbamicAcid

The title compound is prepared by the procedure of Example 33, using theproduct of Example 24.

EXAMPLE 386S-(6aalpha,10alpha)!8-(Aminocarbonyl)-10-(dimethylamino)-5,6a,7,10,10a,11,11a,12-octahydro-4,6,6a,9-tetrahydroxy-3-(methoxycarbonyl)amino!5,7-dioxo-2-naphthacenyl EsterTrifluoromethanesulfonic Acid

The title compound is prepared by the procedure of Example 20, using theproduct from Example 23.

EXAMPLE 39 4S-(4alpha,12aalpha)!8-Chloro-4-(dimethylamino)-9-(dimethylamino)oxy!carbonyl!amino!1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide

The title compound is prepared by the procedure of Example 20, using theproduct from Example 10 and dimethylaminoxy chloroformate.

EXAMPLE 40 4S-(4alpha,12aalpha)!8-Chloro-(diethylamino)oxy!carbonyl!amino!4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide

The title compound is prepared by the procedure of Example 20, using theproduct from Example 10 and diethylamino chloroformate.

EXAMPLE 414S-(4α,12aα)!-9-Amino-8-bromo-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamideHydrobromide (1:1)

The title compound is prepared by the procedure of Example 3, using9-azido-6-demethyl-6-deoxytetracycline prepared by the proceduredescribed on J. Am. Chem. Soc., 84:1426-1430 and a solution of hydrogenbromide in acetic acid (30 wt %).

EXAMPLE 424S-(4α,12aα)!-9-Amino-8-bromo-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamineHydrobromide

The title compound is prepared by the procedure of Example 3, using theproduct from Example 2 and a solution of hydrogen bromide in acetic acid(30 wt %).

EXAMPLE 434S-(4alpha,12aalpha)!9-Amino-4,7-bis(dimethylamino)-8-iodo-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamideHydroiodide

The title compound is prepared by the procedure of Example 3, using theproduct from Example 2 and hydroiodic acid.

EXAMPLE 444S-(4alpha,12aalpha)!9-Amino-4-(dimethylamino)-8-iodo-1,4,4a,5,5a,11,12,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamineHydroiodide

The title compound is prepared by the procedure of Example 3, using9-azido-6-demethyl-6-deoxytetracycline prepared by the proceduredescribed on J. Am. Chem. Soc., 84:1426-1430 and hydroiodic acid.

EXAMPLE 45 7S-(7alpha,10aalpha)!9-(Aminocarbonyl)-7-(dimethylamino)-3-iodo-5,5a,6,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthacenyl!carbamicAcid Methyl Ester

The title compound is prepared by the procedure of Example 20, using theproduct from Example 44.

EXAMPLE 46 7S-(7alpha,10aalpha)!9-(Aminocarbonyl)-3-bromo-7-(dimethylamino)-5,5a,6,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthacenyl!carbamicAcid Methyl Ester

The title compound is prepared by the procedure of Example 20, using theproduct from Example 41.

We claim:
 1. A compound of the formula: ##STR225## wherein Y is selectedfrom --N₂ ⁺ Cl⁻ or N₃ ;X is selected from halogen ortrifluoromethanesulfonyloxy; the halogen is selected from bromine,chlorine, fluorine or iodine; R or R¹ is selected from nitro; amino;halogen selected from chlorine, bromine, fluorine, or iodine; cyano;hydroxy; or --NR² R³ ; R² is selected from hydrogen, methyl, ethyl,n-propyl, 1-methylethyl, n-butyl, and 1-methylpropyl; R³ is selectedfrom methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl, 1,1-dimethylethyl, R⁴ (CH₂)_(n) CO-- or R^(4') (CH₂)_(n)SO₂ --; where n=0-4;with the proviso that when R or R¹ =--NR² R³ and R²=hydrogen, R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, R⁴ (CH₂)_(n) CO-- orR^(4') (CH₂)_(n) SO₂ --;and when R² =methyl or ethyl, R³ =methyl, ethyl,n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl;andwhen R² =n-propyl, R³ =n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,or 2-methylpropy;and when R² =1-methylethyl, R³ =n-butyl,1-methylpropyl, or 2-methylpropy;and when R² =n-butyl, R³ =n-butyl,1-methylpropyl, or 2-methylpropy;and when R² =1-methylpropyl, R³=2-methylpropyl;and when R³ is selected from R⁴ (CH₂)_(n) CO-- and n=0,R⁴ is selected from hydrogen; amino; hydroyamino; straight or branchedmono(C₁ -C₆)alkylamino group where (C₁ -C₆)alkyl is selected frommethyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 2-methylbutyl,1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl, n-hexyl,1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl,1,2-dimethylbutyl, 1,3-dimethylbutyl, 1-methyl-1-ethylpropyl and thediastereomers and enantiomers of said straight or branched mono(C₁-C₆)alkylamino group; (C₃ -C₈)cycloalkylamino group where (C₃-C₈)cycloalkyl is selected from cyclopropyl,trans-1,2-dimethylcyclopropyl, cis-1,2-dimethylcyclopropyl,trans-2,3-dimethylcyclopropyl, cis-2,3-dimethylcyclopropyl, cyclobutyl,trans-2,3-dimethylcyclobutyl, cis-2,3-dimethylcyclobutyl, cyclopentyl,cyclohexyl, cycloheptyl, cyclooctyl, bicyclo 2.2.1!hept-2-yl, bicyclo2.2.2!oct-2-yl and the diastereomers and enantiomers of said (C₃-C₈)cycloalkylamino group; straight or branched chain di-(C₁-C₆)alkylamino group selected from dimethylamino, diethylamino,methyl(ethyl)amino, ethyl(1-methylethyl)amino or where each (C₁-C₆)alkyl is independently selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 1-methyl-ethylpropyl and the diastereomers andenantiomers of said straight or branched chain di-(C₁ -C₆)alkylaminogroup; (C₁ -C₆)alkoxyamino group where (C₁ -C₆)alkoxy is selected frommethoxy, ethoxy, propoxy, butoxy, pentoxy, or hexoxy; (C₃-C₈)cycloalkoxyamino group where (C₃ -C₈)alkoxy is selected fromcyclopropoxy, trans-1,2-dimethylcyclopropoxy,cis-1,2-dimethylcyclopropoxy, trans-2,3-dimethylcyclopropoxy,cis-2,3-dimethylcyclopropoxy, cyclobutoxy,trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, bicyclo 2.2.1!oct-2-yloxy and the diastereomers andenantiomers of said (C₃ -C₈)cycloalkyloxyamino group; (C₇ -C₁₀l)aralkoxyamino group where (C₇ -C₁₀) is selected from benzyloxy,2-phenylethoxy, α-phenylethoxy, (2-naphthyl)methoxy,(1-naphthyl)methoxy, or phenylpropoxy; (C₂ -C₈)azacycloalkyl groupselected from aziridinyl, azetidinyl, pyrrolidinyl, pyrrolinyl,piperidinyl, 2-methylpyrrolidinyl, cis-3,4-dimethylpyrrolidinyl,trans-3,4-dimethylpyrrolidinyl, 2-azabicyclo 2.1.1!hex-2-yl,5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo 2.2.1!hept-2-yl, 7-azabicyclo2.2.1!hept-2-yl, 2-azabicyclo 2.2.2!oct-2-yl and the diastereomers andenantiomers of said (C₂ -C₈)azacycloalkyl group; azaheterocycloalkylgroup selected from morpholinyl, piperazinyl, 4-methylpiperazinyl,4-hydroxypiperazinyl, 4-(C₁ -C₄)alkoxy-piperazinyl, thiamorphinyl,tetrahydro-1,2-oxazinyl, isoxazolidinyl, pyrazolidinyl,2-methylpyrazolidinyl, 2,5-diazabicyclo 2.2.2!hept-2-yl,2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl, and diastereomers andenantiomers of said azaheterocycloalkyl group; (C₆ -C₁₀)arylamino groupselected from phenylamino or naphthylamino; (C₇ -C₁₀)aralkylamino groupwhere (C₇ -C₁₀)aralkyl is selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl, or phenylpropyl;straight or branched (C₁ -C₄)alkyl group selected from methyl, ethyl,n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, or1,1-dimethylethyl; (C₃ -C₆)cycloalkyl group selected from cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl; substituted (C₃ -C₆)cycloalkylgroup where the substitution is selected from (C₁ -C₃)alkyl, cyano,amino or (C₁ -C₃)acyl; (C₆ -C₁₀)aryl group selected from phenyl,α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl group where thesubstitution is selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁-C₃)alkyl, nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁-C₃)alkylamino or carboxy; (C₇ -C₉)aralkyl group selected from benzyl,1-phenylethyl, 2-phenylethyl, or phenylpropyl; α-hydroxy-(C₁ -C₃)alkylgroup selected from hydroxymethyl, α-hydroxyethyl,α-hydroxy-1-methylethyl, or α-hydroxypropyl; α-mercapto(C₁ -C₃)alkylgroup selected from mercaptomethyl, α-mercaptoethyl,α-mercapto-1-methylethyl, or α-mercaptopropyl; halo(C₁ -C₃)alkyl group;a heterocycle group selected from a five membered aromatic or saturatedring with one N, O, S or Se heteroatom, optionally having a benzo orpyrido ring fused thereto, selected from ##STR226## where Z=N, O, S orSe; or a five membered aromatic ring with two N, O, S or Se heteroatoms,optionally having a benzo or pyrido ring fused thereto, selected from##STR227## wherein Z and Z¹ are independently N, O, S or Se; or a fivemembered saturated ring with one or two N, O, S or Se heteroatoms and anadjacent appended O heteroatom selected from ##STR228## wherein A isselected from hydrogen; straight or branched (C₁ -C₄)alkyl; C₆ -aryl;substituted C₆ -aryl where the substitution is selected from halo, (C₁-C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy; (C₇ -C₉)aralkyl groupselected from benzyl, 1-phenylethyl, 2-phenylethyl or phenylpropyl; or asix membered aromatic ring with one to three N heteroatoms, or a sixmembered saturated ring with one or two N, O, S, or Se heteroatoms andan adjacent appended O heteroatom; acyl or haloacyl group selected fromacetyl, propionyl, chloroacetyl, trifluoroacetyl, (C₃-C₆)cycloalkylcarbonyl, (C₆ -C₁₀)aroyl selected from benzoyl ornaphthoyl, halo substituted (C₆ -C₁₀)aroyl, (C₁ -C₄)alkylbenzoyl, or(heterocycle)carbonyl, the heterocycle selected from a five memberedaromatic or saturated ring with one N, O, S or Se heteroatom, optionallyhaving a benzo or pyrido ring fused thereto, selected from ##STR229##where Z=N, O, S or Se; or a five membered aromatic ring with two N, O, Sor Se heteroatoms, optionally having a benzo or pyrido ring fusedthereto, selected from ##STR230## wherein Z and Z¹ are independently N,O, S or Se; or a five membered saturated ring with one or two N, O, S orSe heteroatoms and an adjacent appended O heteroatom selected from##STR231## wherein A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl where the substitution isselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy; (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl; or a six membered aromatic ring with one to three Nheteroatoms, or a six membered saturated ring with one or two N, O, S,or Se heteroatoms and an adjacent appended O heteroatom; (C₁-C₄)alkoxycarbonyl group selected from methoxycarbonyl, ethoxycarbonyl,straight or branched propoxycarbonyl, straight butoxycarbonyl, orallyloxycarbonyl; vinyl or substituted vinyl group where thesubstitution is selected from (C₁ -C₃)alkyl group, halogen, (C₆-C₁₀)aryl group selected from phenyl, α-naphthyl, β-naphthyl,substituted (C₆ -C₁₀)aryl group where the substitution is selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy; halo(C₁ -C₃)alkylgroup, a heterocycle group selected from a five membered aromatic orsaturated ring with one N, O, S or Se heteroatom, optionally having abenzo or pyrido ring fused thereto, selected from ##STR232## where Z=N,O, S or Se; (C₁ -C₄)alkoxy group; C₆ -aryloxy group selected fromphenoxy or substituted phenoxy where the substitution is selected fromhalo, (C₁ -C₄)alkyl, nitro, cyano, thiol, amino, carboxy, or di-(C₁-C₃)alkylamino; (C₇ -C₁₀)aralkoxy group; vinyloxy or substitutedvinyloxy group where the substitution is selected from (C₁ -C₄)alkyl,cyano, carboxy or (C₆ -C₁₀)aryl selected from phenyl, α-naphthyl orβ-naphthyl; R^(a) R^(b) amino(C₁ -C₄)alkoxy group or R^(a) R^(b) aminoxygroup, wherein R^(a) R^(b) is a straight or branched (C₁ -C₄)alkylselected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, (CH₂)_(n) wheren=2-6, or --(CH₂)₂ W(CH₂)₂ -- where W is selected from --N(C₁ -C₃)alkylwhere the alkyl is straight or branched, --NH, O, S, or --NOB where B isselected from hydrogen or (C₁ -C₄)alkyl;and when R³ =R⁴ (CH₂)_(n) CO--and n=1-4, R⁴ is selected from hydrogen; straight or branched (C₁-C₄)alkyl group selected from methyl, ethyl, n-propyl, 1-methylethyl,n-butyl, 1-methylpropyl, 2-methylpropyl, or 1,1-dimethylethyl; (C₃-C₆)cycloalkyl group selected from cyclopropyl, cyclobutyl, cyclopentyl,or cyclohexyl; substituted (C₃ -C₆)cycloalkyl group where thesubstitution is selected from (C₁ -C₃)alkyl, cyano, amino or (C₁-C₃)acyl; (C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl orβ-naphthyl; substituted (C₆ -C₁₀)aryl group where the substitution isselected from halo, (C_(1-C) ₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro,amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy; (C₇-C₉)aralkyl group; acyloxy or haloacyloxy group where acyl or haloacylis selected from acetyl, propionyl, chloroacetyl, trichloroacetyl, (C₃-C₆)cycloalkylcarbonyl, (C₆ -C₁₀)aroyl selected from benzoyl ornaphthoyl, halo substituted(C₆ -C₁₀)aroyl, (C₁ -C₄)alkylbenzoyl,(heterocycle)carbonyl, the heterocycle selected froma five memberedaromatic or saturated ring with one N, O, S or Se heteroatom, optionallyhaving a benzo or pyrido ring fused thereto, selected from ##STR233##where Z=N, O, S or Se; or a five membered aromatic ring with two N, O, Sor Se heteroatoms, optionally having a benzo or pyrido ring fusedthereto, selected from ##STR234## wherein Z and Z¹ are independently N,O, S or Se; or a five membered saturated ring with one or two N, O, S orSe heteroatoms and an adjacent appended O heteroatom selected from##STR235## wherein A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl where the substitution isselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy; (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl; or a six membered aromatic ring with one to three Nheteroatoms, or a six membered saturated ring with one or two N, O, S,or Se heteroatoms and an adjacent appended O heteroatom; (C₁ -C₄)alkoxygroup; C₆ -aryl group selected from phenoxy or substituted phenoxy wherethe substitution is selected from halo, (C₁ -C₄)alkyl, nitro, cyano,thiol, amino, carboxy, or di-(C₁ -C₃)alkylamino; (C₇ -C₁₀)aralkoxygroup; (C₁ -C₃)alkylthio group selected from methylthio, ethylthio,propylthio or allylthio; C₆ -arylthio group selected from phenylthio orsubstituted phenylthio where the substitution is selected from halo (C₁-C₄)alkyl, nitro, cyano, thio, amino, carboxy, di-(C₁ -C₃)alkylamino; C₆-arylsulfonyl group selected from phenylsulfonyl or substitutedphenylsulfonyl where the substitution is selected from halo, (C₁-C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy; (C₇ -C₈)aralkylthiogroup; a heterocycle group selected from a five membered aromatic orsaturated ring with one N, O, S or Se heteroatom, optionally having abenzo or pyrido ring fused thereto, selected from ##STR236## where Z=N,O, S or Se; or a five membered aromatic ring with two N, O, S or Seheteroatoms, optionally having a benzo or pyrido ring fused thereto,selected from ##STR237## wherein Z and Z¹ are independently N, O, S orSe; or a five membered saturated ring with one or two N, O, S or Seheteroatoms and an adjacent appended O heteroatom selected from##STR238## wherein A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl where the substitution isselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy; (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl; or a six membered aromatic ring with one to three Nheteroatoms, or a six membered saturated ring with one or two N, O, S,or Se heteroatoms and an adjacent appended O heteroatom; hydroxy group,mercapto group; α-hydroxy(C₁ -C₃)alkyl group selected from hydroxymethy,α-hydroxyethyl, α-hydroxy-1-methylethyl or α-hydroxypropyl; halo(C₁-C₃)alkyl group; acyl or haloacyl group selected from acetyl, propionyl,chloroacetyl, trifluoroacetyl, (C₃ -C₆)cycloalkylcarbonyl, (C₆-C₁₀)aroyl selected from benzoyl or naphthoyl, halo substituted (C₆-C₁₀)aroyl, (C₁ -C₄)alkylbenzoyl, or (heterocycle)carbonyl, theheterocycle selected from a five membered aromatic or saturated ringwith one N, O, S or Se heteroatom, optionally having a benzo or pyridoring fused thereto, selected from ##STR239## where Z=N, O, S or Se; or afive membered aromatic ring with two N, O, S or Se heteroatoms,optionally having a benzo or pyrido ring fused thereto, selected from##STR240## wherein Z and Z¹ are independently N, O, S or Se; or a fivemembered saturated ring with one or two N, O, S or Se heteroatoms and anadjacent appended O heteroatom selected from ##STR241## wherein A isselected from hydrogen; straight or branched (C₁ -C₄)alkyl; C₆ -aryl;substituted C₆ -aryl where the substitution is selected from halo, (C₁-C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy; (C₇ -C₉)aralkyl groupselected from benzyl, 1-phenylethyl, 2-phenylethyl or phenylpropyl; or asix membered aromatic ring with one to three N heteroatoms, or a sixmembered saturated ring with one or two N, O, S, or Se heteroatoms andan adjacent appended O heteroatom; (C₁ -C₄)alkoxycarbonyl group selectedfrom methoxycarbonyl, ethoxycarbonyl, straight or branchedpropoxycarbonyl, allyloxycarbonyl, or straight or branchedbutoxycarbonyl; R^(a) R^(b) amino(C₁ -C₄)alkoxy group or R^(a) R^(b)aminoxy group, wherein R^(a) R^(b) is a straight or branched (C₁-C₄)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, (CH₂)_(n) wheren=2-6, or --(CH₂)₂ W(CH₂)₂ -- where W is selected from --N(C₁ -C₃)alkylwhere the alkyl is straight or branched, --NH, O, S, or --NOB where B isselected from hydrogen or (C₁ -C₄)alkyl;and when R³ =R⁴ (CH₂)_(n) CO--and n=2-4, R⁴ is additionally selected from amino; hydroyamino; straightor branched mono(C₁ -C₆)alkylamino group where (C₁ -C₆)alkyl is selectedfrom methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 2-methylbutyl,1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl, n-hexyl,1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl,1,2-dimethylbutyl, 1-methyl-1-ethylpropyl and the diastereomers andenantiomers of said straight or branched mono(C₁ -C₆)alkylamino group;(C₃ -C₈)cycloalkylamino group where (C₃ -C₈)cycloalkyl is selected fromcyclopropyl, trans-1,2-dimethylcyclopropyl, cis-1,2-dimethylcyclopropyl,trans-2,3-dimethylcyclopropyl, cis-2,3-dimethylcyclopropyl, cyclobutyl,trans-2,3-dimethylcyclobutyl, cis-2,3-dimethylcyclobutyl, cyclopentyl,cyclohexyl, cycloheptyl, cyclooctyl, bicyclo 2.2.1!hept-2-yl, bicyclo2.2.2!oct-2-yl and the diastereomers and enantiomers of said (C₃-C₈)cycloalkylamino group; straight or branched chain di-(C₁-C₆)alkylamino group selected from dimethylamino, diethylamino,methyl(ethyl)amino, ethyl(1-methylethyl)amino or where each (C₁-C₆)alkyl is independently selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 1-methyl-ethylpropyl and the diastereomers andenantiomers of said straight or branched chain di-(C₁ -C₆)alkylaminogroup; (C₁ -C₆)alkoxyamino group where (C₁ -C₆)alkoxy is selected frommethoxy, ethoxy, propoxy, butoxy, pentoxy, or hexoxy; (C₃-C₈)cycloalkoxyamino group where (C₃ -C₈)alkoxy is selected fromcyclopropoxy, trans-1,2-dimethylcyclopropoxy,cis-1,2-dimethylcyclopropoxy, trans-2,3-dimethylcyclopropoxy,cis-2,3-dimethylcyclopropoxy, cyclobutoxy,trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, bicyclo 2.2.1!oct-2-yloxy and the diastereomers andenantiomers of said (C₃ -C₈)cycloalkyloxyamino group; (C₇-C₁₀)aralkoxyamino group where (C₇ -C₁₀) is selected from benzyloxy,2-phenylethoxy, α-phenylethoxy, (2-naphthyl)methoxy,(1-naphthyl)methoxy, or phenylpropoxy; (C₂ -C₈)azacycloalkyl groupselected from aziridinyl, azetidinyl, pyrrolidinyl, pyrrolinyl,piperidinyl, 2-methylpyrrolidinyl, cis-3,4-dimethylpyrrolidinyl,trans-3,4-dimethylpyrrolidinyl, 2-azabicyclo 2.1.1!hex-2-yl,5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo 2.2.1!hept-2-yl, 7-azabicyclo2.2.1!hept-2-yl, 2-azabicyclo 2.2.2!oct-2-yl and the diastereomers andenantiomers of said (C₂ -C₈)azacycloalkyl group; azaheterocycloalkylgroup selected from morpholinyl, piperazinyl, 4-methylpiperazinyl,4-hydroxypiperazinyl, 4-(C₁ -C₄)alkoxy-piperazinyl, thiamorphinyl,tetrahydro-1,2-oxazinyl, isoxazolidinyl, pyrazolidinyl,2-methylpyrazolidinyl, 2,5-diazabicyclo 2.2.2!hept-2-yl,2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl, and diastereomers andenantiomers of said azaheterocycloalkyl group; (C₆ -C₁₀)arylamino groupselected from phenylamino or naphthylamino; (C₇ -C₁₀)aralkylamino groupwhere (C₇ -C₁₀)aralkyl is selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl, or phenylpropyl;(C₁ -C₄)alkoxycarbonylamino group selected from n-butoxycarbonylamino,allyloxycarbonylamino, methoxycarbonylamino, ethoxycarbonylamino, orpropoxycarbonylamino;and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=0,R^(4') is selected from amino; hydroyamino; straight or branched mono(C₁-C₆)alkylamino group where (C₁ -C₆)alkyl is selected from methyl, ethyl,n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 1-methyl-1-ethylpropyl and the diastereomers andenantiomers of said straight or branched mono(C₁ -C₆)alkylamino group;(C₃ -C₈)cycloalkylamino group where (C₃ -C₈)cycloalkyl is selected fromcyclopropyl, trans-1,2-dimethylcyclopropyl, cis-1,2-dimethylcyclopropyl,trans-2,3-dimethylcyclopropyl, cis-2,3-dimethylcyclopropyl, cyclobutyl,trans-2,3-dimethylcyclobutyl, cis-2,3-dimethylcyclobutyl, cyclopentyl,cyclohexyl, cycloheptyl, cyclooctyl, bicyclo 2.2.1!hept-2-yl, bicyclo2.2.2!oct-2-yl and the diastereomers and enantiomers of said (C₃-C₈)cycloalkylamino group; straight or branched chain di-(C₁-C₆)alkylamino group selected from dimethylamino, diethylamino,methyl(ethyl)amino, ethyl(1-methylethyl)amino or where each (C₁-C₆)alkyl is independently selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 1-methyl-ethylpropyl and the diastereomers andenantiomers of said straight or branched chain di-(C₁ -C₆)alkylaminogroup; (C₁ -C₆)alkoxyamino group where (C₁ -C₆)alkoxy is selected frommethoxy, ethoxy, propoxy, butoxy, pentoxy, or hexoxy; (C₃-C₈)cycloalkoxyamino group where (C₃ -C₈)alkoxy is selected fromcyclopropoxy, trans-1,2-dimethylcyclopropoxy, cis-1,2-dimethylcyclopropoxy, trans-2,3-dimethylcyclopropoxy,cis-2,3-dimethylcyclopropoxy, cyclobutoxy,trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, bicyclo 2.2.1!oct-2-yloxy and the diastereomers andenantiomers of said (C₃ -C₈)cycloalkyloxyamino group; (C₇-C₁₀)aralkoxyamino group where (C₇ -C₁₀) is selected from benzyloxy,2-phenylethoxy, α-phenylethoxy, (2-naphthyl)methoxy,(1-naphthyl)methoxy, or phenylpropoxy; straight or branched (C₁-C₄)alkyl group selected from methyl, ethyl, n-propyl, 1-methylethyl,n-butyl, 1-methylpropyl, 2-methylpropyl, or 1,1-dimethylethyl; (C₃-C₆)cycloalkyl group selected from cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl; substituted (C₃ -C₆)cycloalkyl group where the substitutionis selected from (C₁ -C₃)alkyl, cyano, amino or (C₁ -C₃)acyl; (C₆-C₁₀)aryl group selected from phenyl, α-naphthyl or, β-naphthyl;substituted (C₆ -C₁₀)aryl group where the substitution is selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy; (C₇ -C₉)aralkylgroup; halo (C₁ -C₃)alkyl group; a heterocycle group selected froma fivemembered aromatic or saturated ring with one N, O, S or Se heteroatom,optionally having a benzo or pyrido ring fused thereto, selected from##STR242## where Z=N, O, S or Se; or a five membered aromatic ring withtwo N, O, S or Se heteroatoms, optionally having a benzo or pyrido ringfused thereto, selected from ##STR243## wherein Z and Z¹ areindependently N, O, S or Se; or a five membered saturated ring with oneor two N, O, S or Se heteroatoms and an adjacent appended O heteroatomselected from ##STR244## wherein A is selected from hydrogen; straightor branched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆ -aryl where thesubstitution is selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁-C₃)alkyl, nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁-C₃)alkylamino or carboxy; (C₇ -C₉)aralkyl group selected from benzyl,1-phenylethyl, 2-phenylethyl or phenylpropyl; or a six membered aromaticring with one to three N heteroatoms, or a six membered saturated ringwith one or two N, O, S, or Se heteroatoms and an adjacent appended Oheteroatom; R^(a) R^(b) amino(C₁ -C₄)alkoxy group or R^(a) R^(b) aminoxygroup, wherein R^(a) R^(b) is a straight or branched (C₁ -C₄)alkylselected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, (CH₂)_(n) wheren=2-6, or --(CH₂)₂ W(CH₂)₂ -- where W is selected from --N(C₁ -C₃)alkylwhere the alkyl is straight or branched, --NH, O, S, or --NOB where B isselected from hydrogen or (C₁ -C₄)alkyl;and when R³ =R^(4') (CH₂)_(n)SO₂ -- and n=1-4, R^(4') is selected from hydrogen; amino; straight orbranched (C₁ -C₄)alkyl group selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, or1,1-dimethylethyl; (C₁ -C₄)carboxyalkyl; (C₃ -C₆)cycloalkyl groupselected from cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl;substituted (C₃ -C₆)cycloalkyl group where the substitution is selectedfrom (C₁ -C₃)alkyl, cyano, amino or (C₁ -C₃)acyl; (C₆ -C₁₀)aryl groupselected from phenyl, α-naphthyl or β-naphthyl; substituted (C₆-C₁₀)aryl group where the substitution is selected from halo, (C₁-C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy; (C₇ -C₉)aralkyl groupselected from benzyl, 1-phenylethyl, 2-phenylethyl, or phenylpropyl; (C₁-C₄)alkoxy group; C₆ -aryloxy group selected from phenoxy or substitutedphenoxy where the substitution is selected from halo, (C₁ -C₄)alkyl,nitro, cyano, thiol, amino, carboxy, or di-(C₁ -C₃)alkylamino; (C₇-C₁₀)aralkoxy group; R^(a) R^(b) amino(C₁ -C₄)alkoxy group or R^(a)R^(b) aminoxy group, wherein R^(a) R^(b) is a straight or branched (C₁-C₄)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, (CH₂)_(n) wheren=2-6, or --(CH₂)₂ W(CH₂)₂ -- where W is selected from --N(C₁ -C₃)alkylwhere the alkyl is straight or branched, --NH, O, S, or --NOB where B isselected from hydrogen or (C₁ -C₄)alkyl; (C₁ -C₃)alkylthio groupselected from methylthio, ethylthio, or n-propylthio; C₆ -arylthio groupselected from phenylthio or substituted phenylthio where thesubstitution is selected from halo (C₁ -C₄)alkyl, nitro, cyano, thio,amino, carboxy, di-(C₁ -C₃)alkylamino; (C₇ -C₈)aralkylthio group; aheterocycle group selected from a five membered aromatic or saturatedring with one N, O, S or Se heteroatom, optionally having a benzo orpyrido ring fused thereto, selected from ##STR245## where Z=N, O, S orSe; or a five membered aromatic ring with two N, O, S or Se heteroatoms,optionally having a benzo or pyrido ring fused thereto, selected from##STR246## wherein Z and Z¹ are independently N, O, S or Se; or a fivemembered saturated ring with one or two N, O, S or Se heteroatoms and anadjacent appended O heteroatom selected from ##STR247## wherein A isselected from hydrogen; straight or branched (C₁ -C₄)alkyl; C₆ -aryl;substituted C₆ -aryl where the substitution is selected from halo, (C₁-C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy; (C₇ -C₉)aralkyl groupselected from benzyl, 1-phenylethyl, 2-phenylethyl or phenylpropyl; or asix membered aromatic ring with one to three N heteroatoms, or a sixmembered saturated ring with one or two N, O, S, or Se heteroatoms andan adjacent appended O heteroatom; hydroxy group; mercapto group; halo(C₁ -C₃)alkyl group; acyl or haloacyl group selected from acetyl,propionyl, chloroacetyl, trifluoroacetyl, (C₃ -C₆)cycloalkylcarbonyl,(C₆ -C₁₀)aroyl selected from benzoyl or naphthoyl, halo substituted (C₆-C₁₀)aroyl, (C₁ -C₄)alkylbenzoyl, or (heterocycle)carbonyl, theheterocycle selected from a five membered aromatic or saturated ringwith one N, O, S or Se heteroatom, optionally having a benzo or pyridoring fused thereto, selected from ##STR248## where Z=N, O, S or Se; or afive membered aromatic ring with two N, O, S or Se heteroatoms,optionally having a benzo or pyrido ring fused thereto, selected from##STR249## wherein Z and Z¹ are independently N, O, S or Se; or a fivemembered saturated ring with one or two N, O, S or Se heteroatoms and anadjacent appended O heteroatom selected from ##STR250## wherein A isselected from hydrogen; straight or branched (C₁ -C₄)alkyl; C₆ -aryl;substituted C₆ -aryl where the substitution is selected from halo, (C₁-C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy; (C₇ -C₉)aralkyl groupselected from benzyl, 1-phenylethyl, 2-phenylethyl or phenylpropyl; or asix membered aromatic ring with one to three N heteroatoms, or a sixmembered saturated ring with one or two N, O, S, or Se heteroatoms andan adjacent appended O heteroatom; (C₁ -C₄)alkoxycarbonyl group selectedfrom methoxycarbonyl, ethoxycarbonyl, straight or branchedpropoxycarbonyl, allyloxycarbonyl or straight butoxycarbonyl; or apharmacologically acceptable organic or inorganic salt or metal complexthereof.
 2. A compound according to claim 1, (whereinY is selected from--N₂ ⁺ Cl⁻ or N₃ ; X is selected from halogen ortrifluoromethanesulfonyloxy; the halogen is selected from bromine,chlorine, fluorine or iodine; R or R¹ is selected from nitro; amino;halogen selected from chlorine, bromine, fluorine, or iodine; cyano;hydroxy; or --NR² R³ ; R² is selected from hydrogen, methyl, ethyl,n-propyl, 1-methylethyl, n-butyl, and 1-methylpropyl; R³ is selectedfrom methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl, 1,1-dimethylethyl, R⁴ (CH₂)_(n) CO-- or R^(4') (CH₂)_(n)SO₂ --; where n=0-4;with the proviso that when R or R¹ =--NR² R³ and R²=hydrogen, R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, R⁴ (CH₂)_(n) CO-- orR^(4') (CH₂)_(n) SO₂ --;and when R³ is selected from R⁴ (CH₂)_(n) CO--and n=0, R⁴ is selected from hydrogen; amino; hydroyamino; straight orbranched mono(C₁ -C₆)alkylamino group where (C₁ -C₆)alkyl is selectedfrom methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 2-methylbutyl,1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl, n-hexyl,1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl,1,2-dimethylbutyl, 1,3-dimethylbutyl, 1-methyl-1-ethylpropyl and thediastereomers and enantiomers of said straight or branched mono(C₁-C₆)alkylamino group; (C₃ -C₈)cycloalkylamino group where (C₃-C₈)cycloalkyl is selected from cyclopropyl,trans-1,2-dimethylcyclopropyl, cis-1,2-dimethylcyclopropyl,trans-2,3-dimethylcyclopropyl, cis-2,3-dimethylcyclopropyl, cyclobutyl,trans-2,3-dimethylcyclobutyl, cis-2,3-dimethylcyclobutyl, cyclopentyl,cyclohexyl, cycloheptyl, cyclooctyl, bicyclo 2.2.1!hept-2-yl, bicyclo2.2.2!oct-2-yl and the diastereomers and enantiomers of said (C₃-C₈)cycloalkylamino group; straight or branched chain di-(C₁-C₆)alkylamino group selected from dimethylamino, diethylamino,methyl(ethyl)amino, ethyl(1-methylethyl)amino or where each (C₁-C₆)alkyl is independently selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 1-methyl-ethylpropyl and the diastereomers andenantiomers of said straight or branched chain di-(C₁ -C₆)alkylaminogroup; (C₁ -C₆)alkoxyamino group where (C₁ -C₆)alkoxy is selected frommethoxy, ethoxy, propoxy, butoxy, pentoxy, or hexoxy; (C₃-C₈)cycloalkoxyamino group where (C₃ -C₈)alkoxy is selected fromcyclopropoxy, trans-1,2-dimethylcyclopropoxy,cis-1,2-dimethylcyclopropoxy, trans-2,3-dimethylcyclopropoxy,cis-2,3-dimethylcyclopropoxy, cyclobutoxy,trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, bicyclo 2.2.1!oct-2-yloxy and the diastereomers andenantiomers of said (C₃ -C₈)cycloalkyloxyamino group; (C₇-C₁₀)aralkoxyamino group where (C₇ -C₁₀) is selected from benzyloxy,2-phenylethoxy, α-phenylethoxy, (2-naphthyl)methoxy,(1-naphthyl)methoxy, or phenylpropoxy; (C₂ -C₈)azacycloalkyl groupselected from aziridinyl, azetidinyl, pyrrolidinyl, pyrrolinyl,piperidinyl, 2-methylpyrrolidinyl, cis-3,4-dimethylpyrrolidinyl,trans-3,4-dimethylpyrrolidinyl, 2-azabicyclo 2.1.1!hex-2-yl,5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo 2.2.1!hept-2-yl, 7-azabicyclo2.2.1!hept-2-yl, 2-azabicyclo 2.2.2!oct-2-yl and the diastereomers andenantiomers of said (C₂ -C₈)azacycloalkyl group; azaheterocycloalkylgroup selected from morpholinyl, piperazinyl, 4-methylpiperazinyl,4-hydroxypiperazinyl, 4-(C₁ -C₄)alkoxy-piperazinyl, thiamorphinyl,tetrahydro-1,2-oxazinyl, isoxazolidinyl, pyrazolidinyl,2-methylpyrazolidinyl, 2,5-diazabicyclo 2.2.2!hept-2-yl,2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl, and diastereomers andenantiomers of said azaheterocycloalkyl group; (C₆ -C₁₀)arylamino groupselected from phenylamino or naphthylamino; (C₇ -C₁₀)aralkylamino groupwhere (C₇ -C₁₀)aralkyl is selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl, or phenylpropyl;straight or branched (C₁ -C₃)alkyl group selected from methyl, ethyl,n-propyl, or 1-methylethyl; (C₃ -C₆)cycloalkyl group selected fromcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl; substituted (C₃-C₆)cycloalkyl group where the substitution is selected from (C₁-C₃)alkyl, cyano, amino or (C₁ -C₃)acyl; (C₆ -C₁₀)aryl group selectedfrom phenyl, α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl groupwhere the substitution is selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁-C₃)alkyl, nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁-C₃)alkylamino or carboxy; α-hydroxy-(C₁ -C₃)alkyl group selected fromhydroxymethyl, α-hydroxyethyl, α-hydroxy-1-methylethyl, orα-hydroxypropyl; halo(C₁ -C₃)alkyl group; a heterocycle group selectedfrom a five membered aromatic or saturated ring with one N, O, S or Seheteroatom, optionally having a benzo or pyrido ring fused thereto,selected from ##STR251## where Z=N, O, S or Se; or a five memberedaromatic ring with two N, O, S or Se heteroatoms, optionally having abenzo or pyrido ring fused thereto, selected from ##STR252## wherein Zand Z¹ are independently N, O, S or Se; or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom selected from ##STR253## wherein A is selected fromhydrogen; straight or branched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆-aryl where the substitution is selected from halo, (C₁ -C₄)alkoxy,trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁-C₃)alkylamino or carboxy; (C₇ -C₉)aralkyl group selected from benzyl,1-phenylethyl, 2-phenylethyl or phenylpropyl; or a six membered aromaticring with one to three N heteroatoms, or a six membered saturated ringwith one or two N, O, S, or Se heteroatoms and an adjacent appended Oheteroatom; acyl or haloacyl group selected from acetyl, propionyl,chloroacetyl, trifluoroacetyl, (C₃ -C₆)cycloalkylcarbonyl, (C₆-C₁₀)aroyl selected from benzoyl or naphthoyl, halo substituted (C₆-C₁₀)aroyl, (C₁ -C₄)alkylbenzoyl, or (heterocycle)carbonyl, theheterocycle selected from a five membered aromatic or saturated ringwith one N, O, S or Se heteroatom, optionally having a benzo or pyridoring fused thereto, selected from ##STR254## where Z=N, O, S or Se; or afive membered aromatic ring with two N, O, S or Se heteroatoms,optionally having a benzo or pyrido ring fused thereto, selected from##STR255## wherein Z and Z¹ are independently N, O, S or Se; or a fivemembered saturated ring with one or two N, O, S or Se heteroatoms and anadjacent appended O heteroatom selected from ##STR256## wherein A isselected from hydrogen; straight or branched (C₁ -C₄)alkyl; C₆ -aryl;substituted C₆ -aryl where the substitution is selected from halo, (C₁-C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy; (C₇ -C₉)aralkyl groupselected from benzyl, 1-phenylethyl, 2-phenylethyl or phenylpropyl; or asix membered aromatic ring with one to three N heteroatoms, or a sixmembered saturated ring with one or two N, O, S, or Se heteroatoms andan adjacent appended O heteroatom; (C₁ -C₄)alkoxycarbonyl group selectedfrom methoxycarbonyl, ethoxycarbonyl, straight or branchedpropoxycarbonyl, straight butoxycarbonyl, or allyloxycarbonyl; vinyl orsubstituted vinyl group where the substitution is selected from (C₁-C₃)alkyl group, halogen, (C₆ -C₁₀)aryl group selected from phenyl,α-naphthyl, βnaphthyl, substituted (C₆ -C₁₀)aryl group where thesubstitution is selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁-C₃)alkyl, nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁-C₃)alkylamino or carboxy; halo(C₁ -C₃)alkyl group, a heterocycle groupselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom, optionally having a benzo or pyrido ring fusedthereto, selected from ##STR257## where Z=N, O, S or Se; (C₁ -C₄)alkoxygroup; C₆ -aryloxy group selected from phenoxy or substituted phenoxywhere the substitution is selected from halo, (C₁ -C₄)alkyl, nitro,cyano, thiol, amino, carboxy, or di-(C₁ -C₃)alkylamino; (C₇-C₁₀)aralkoxy group; vinyloxy or substituted vinyloxy group where thesubstitution is selected from (C₁ -C₄)alkyl, cyano, carboxy or (C₇-C₁₀)aryl selected from phenyl, α-naphthyl or, β-naphthyl; R^(a) R^(b)amino(C₁ -C₄)alkoxy group or R^(a) R^(b) aminoxy group, wherein R^(a)R^(b) is a straight or branched (C₁ -C₄)alkyl selected from methyl,ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, (CH₂)_(n) where n=2-6, or --(CH₂)₂ W(CH₂)₂ -- where Wis selected from --N(C₁ -C₃)alkyl where the alkyl is straight orbranched, --NH, O, S, or --NOB where B is selected from hydrogen or (C₁-C₄)alkyl;and when R³ =R⁴ (CH₂)_(n) CO-- and n=1-4, R⁴ is selected fromhydrogen; straight or branched (C₁ -C₄)alkyl group selected from methyl,ethyl, n-propyl, or 1-methylethyl; (C₆ -C₁₀)aryl group selected fromphenyl, α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl group wherethe substitution is selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁-C₃)alkyl, nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁-C₃)alkylamino or carboxy; (C₇ -C₉)aralkyl group; acyloxy or haloacyloxygroup where acyl or haloacyl is selected from acetyl, propionyl,chloroacetyl, trichloroacetyl, (C₃ -C₆)cycloalkylcarbonyl, (C₆-C₁₀)aroyl selected from benzoyl or naphthoyl, halo substituted(C₆-C₁₀)aroyl, (C₁ -C₄)alkylbenzoyl, (heterocycle)carbonyl, the heterocycleselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom, optionally having a benzo or pyrido ring fusedthereto, selected from ##STR258## where Z=N, O, S or Se; or a fivemembered aromatic ring with two N, O, S or Se heteroatoms, optionallyhaving a benzo or pyrido ring fused thereto, selected from ##STR259##wherein Z and Z¹ are independently N, O, S or Se; or a five memberedsaturated ring with one or two N, O, S or Se heteroatoms and an adjacentappended O heteroatom selected from ##STR260## wherein A is selectedfrom hydrogen; straight or branched (C₁ -C₄)alkyl; C₆ -aryl;substitutedC₆ -aryl where the substitution is selected from halo, (C₁ -C₄)alkoxy,trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁-C₃)alkylamino or carboxy; (C₇ -C₉)aralkyl group selected from benzyl,1-phenylethyl, 2-phenylethyl or phenylpropyl; or a six membered aromaticring with one to three N heteroatoms, or a six membered saturated ringwith one or two N, O, S, or Se heteroatoms and an adjacent appended Oheteroatom; (C₁ -C₄)alkoxy group; R^(a) R^(b) amino(C₁ -C₄)alkoxy groupor R^(a) R^(b) aminoxy group, wherein R^(a) R^(b) is a straight orbranched (C₁ -C₄)alkyl selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, (CH₂)_(n) where n=2-6, or --(CH₂)₂ W(CH₂)₂ -- where Wis selected from --N(C₁ -C₃)alkyl where the alkyl is straight orbranched, --NH, O, S, or --NOB where B is selected from hydrogen or (C₁-C₄)alkyl; C₆ -aryloxy group selected from phenoxy or substitutedphenoxy where the substitution is selected from halo, (C₁ -C₄)alkyl,nitro, cyano, thiol, amino, carboxy, or di-(C₁ -C₃)alkylamino; (C₁-C₃)alkylthio group selected from methylthio, ethylthio, propylthio orallylthio; C₆ -arylthio group selected from phenylthio or substitutedphenylthio where the substitution is selected from halo (C₁ -C₄)alkyl,nitro, cyano, thio, amino, carboxy, di-(C₁ -C₃)alkylamino; C₆-arylsulfonyl group selected from phenylsulfonyl or substitutedphenylsulfonyl where the substitution is selected from halo, (C₁-C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy; a heterocycle groupselected froma five membered aromatic or saturated ring with one N, O, Sor Se heteroatom, optionally having a benzo or pyrido ring fusedthereto, selected from ##STR261## where Z=N, O, S or Se; or a fivemembered aromatic ring with two N, O, S or Se heteroatoms, optionallyhaving a benzo or pyrido ring fused thereto, selected from ##STR262##wherein Z and Z¹ are independently N, O, S or Se; or a five memberedsaturated ring with one or two N, O, S or Se heteroatoms and an adjacentappended O heteroatom selected from ##STR263## wherein A is selectedfrom hydrogen; straight or branched (C₁ -C₄)alkyl; C₆ -aryl; substitutedC₆ -aryl where the substitution is selected from halo, (C₁ -C₄)alkoxy,trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁-C₃)alkylamino or carboxy; (C₇ -C₉)aralkyl group selected from benzyl,1-phenylethyl, 2-phenylethyl or phenylpropyl; or a six membered aromaticring with one to three N heteroatoms, or a six membered saturated ringwith one or two N, O, S, or Se heteroatoms and an adjacent appended Oheteroatom; hydroxy group; α-hydroxy(C₁ -C₃)alkyl group selected fromhydroxymethy, α-hydroxyethyl, α-hydroxy-1-methylethyl oraα-hydroxypropyl; halo(C₁ -C₃)alkyl group; acyl or haloacyl groupselected from acetyl, propionyl, chloroacetyl, trifluoroacetyl, (C₃-C₆)cycloalkylcarbonyl, (C₆ -C₁₀)aroyl selected from benzoyl ornaphthoyl, halo substituted (C₆ -C₁₀)aroyl, (C₁ -C₄)alkylbenzoyl, or(heterocycle)carbonyl, the heterocycle selected from a five memberedaromatic or saturated ring with one N, O, S or Se heteroatom, optionallyhaving a benzo or pyrido ring fused thereto, selected from ##STR264##where Z=N, O, S or Se; or a five membered aromatic ring with two N, O, Sor Se heteroatoms, optionally having a benzo or pyrido ring fusedthereto, selected from ##STR265## wherein Z and Z¹ are independently N,O, S or Se; or a five membered saturated ring with one or two N, O, S orSe heteroatoms and an adjacent appended O heteroatom selected from##STR266## wherein A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl where the substitution isselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy; (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl; or a six membered aromatic ring with one to three Nheteroatoms, or a six membered saturated ring with one or two N, O, S,or Se heteroatoms and an adjacent appended O heteroatom;and when R³ =R⁴(CH₂)_(n) CO-- and n=2-4, R⁴ is additionally selected from amino;hydroyamino; straight or branched mono(C₁ -C₆)alkylamino group where (C₁-C₆)alkyl is selected from methyl, ethyl, n-propyl, 1-methylethyl,n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,1-methyl-1-ethylpropyl and the diastereomers and enantiomers of saidstraight or branched mono(C₁ -C₆)alkylamino group; (C₃-C₈)cycloalkylamino group where (C₃ -C₈)cycloalkyl is selected fromcyclopropyl, trans-1,2-dimethylcyclopropyl, cis-1,2-dimethylcyclopropyl,trans-2,3-dimethylcyclopropyl, cis-2,3-dimethylcyclopropyl, cyclobutyl,trans-2,3-dimethylcyclobutyl, cis-2,3-dimethylcyclobutyl, cyclopentyl,cyclohexyl, cycloheptyl, cyclooctyl, bicyclo 2.2.1!hept-2-yl, bicyclo2.2.2!oct-2-yl and the diastereomers and enantiomers of said (C₃-C₈)cycloalkylamino group; straight or branched chain di-(C₁-C₆)alkylamino group selected from dimethylamino, diethylamino,methyl(ethyl)amino, ethyl(1-methylethyl)amino or where each (C₁-C₆)alkyl is independently selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 1-methyl-ethylpropyl and the diastereomers andenantiomers of said straight or branched chain di-(C₁ -C₆)alkylaminogroup; (C₁ -C₆)alkoxyamino group where (C₁ -C₆)alkoxy is selected frommethoxy, ethoxy, propoxy, butoxy, pentoxy, or hexoxy; (C₃-C₈)cycloalkoxyamino group where (C₃ -C₈)alkoxy is selected fromcyclopropoxy, trans-1,2-dimethylcyclopropoxy,cis-1,2-dimethylcyclopropoxy, trans-2,3-dimethylcyclopropoxy,cis-2,3-dimethylcyclopropoxy, cyclobutoxy,trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, bicyclo 2.2.1!oct-2-yloxy and the diastereomers andenantiomers of said (C₃ -C₈)cycloalkyloxyamino group; (C₇-C₁₀)aralkoxyamino group where (C₇ -C₁₀) is selected from benzyloxy,2-phenylethoxy, α-phenylethoxy, (2-naphthyl)methoxy,(1-naphthyl)methoxy, or phenylpropoxy; (C₂ -C₈)azacycloalkyl groupselected from aziridinyl, azetidinyl, pyrrolidinyl, pyrrolinyl,piperidinyl, 2-methylpyrrolidinyl, cis-3,4-dimethylpyrrolidinyl,trans-3,4-dimethylpyrrolidinyl, 2-azabicyclo 2.1.1!hex-2-yl,5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo 2.2.1!hept-2-yl, 7-azabicyclo2.2.1!hept-2-yl, 2-azabicyclo 2.2.2!oct-2-yl and the diastereomers andenantiomers of said (C₂ -C₈)azacycloalkyl group; azaheterocycloalkylgroup selected from morpholinyl, piperazinyl, 4-methylpiperazinyl,4-hydroxypiperazinyl, 4-(C₁ -C₄)alkoxy-piperazinyl, thiamorphinyl,tetrahydro-1,2-oxazinyl, isoxazolidinyl, pyrazolidinyl,2-methylpyrazolidinyl, 2,5-diazabicyclo 2.2.2!hept-2-yl,2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl, and diastereomers andenantiomers of said azaheterocycloalkyl group; (C₆ -C₁₀)arylamino groupselected from phenylamino or naphthylamino; (C₇ -C₁₀)aralkylamino groupwhere (C₇ -C₁₀)aralkyl is selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl, or phenylpropyl;(C₁ -C₄)alkoxycarbonylamino group selected from n-butoxycarbonylamino,allyloxycarbonylamino, methoxycarbonylamino, ethoxycarbonylamino, orpropoxycarbonylamino;and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=0,R^(4') is selected from amino; hydroyamino; straight or branched mono(C₁-C₆)alkylamino group where (C₁ -C₆)alkyl is selected from methyl, ethyl,n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 1-methyl-1-ethylpropyl and the diastereomers andenantiomers of said straight or branched mono(C₁ -C₆)alkylamino group;(C₃ -C₈)cycloalkylamino group where (C₃ -C₈)cycloalkyl is selected fromcyclopropyl, trans-1,2-dimethylcyclopropyl, cis-1,2-dimethylcyclopropyl,trans-2,3-dimethylcyclopropyl, cis-2,3-dimethylcyclopropyl, cyclobutyl,trans-2,3-dimethylcyclobutyl, cis-2,3-dimethylcyclobutyl, cyclopentyl,cyclohexyl, cycloheptyl, cyclooctyl, bicyclo 2.2.1!hept-2-yl, bicyclo2.2.2!oct-2-yl and the diastereomers and enantiomers of said (C₃-C₈)cycloalkylamino group; straight or branched chain di-(C₁-C₆)alkylamino group selected from dimethylamino, diethylamino,methyl(ethyl)amino, ethyl(1-methylethyl)amino or where each (C₁-C₆)alkyl is independently selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 1-methyl-ethylpropyl and the diastereomers andenantiomers of said straight or branched chain di-(C₁ -C₆)alkylaminogroup; (C₁ -C₆)alkoxyamino group where (C₁ -C₆)alkoxy is selected frommethoxy, ethoxy, propoxy, butoxy, pentoxy, or hexoxy; (C₃-C₈)cycloalkoxyamino group where (C₃ -C₈)alkoxy is selected fromcyclopropoxy, trans-1,2-dimethylcyclopropoxy,cis-1,2-dimethylcyclopropoxy, trans-2,3-dimethylcyclopropoxy,cis-2,3-dimethylcyclopropoxy, cyclobutoxy,trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, bicyclo 2.2.1!oct-2-yloxy and the diastereomers andenantiomers of said (C₃ -C₈)cycloalkyloxyamino group; (C₇-C₁₀)aralkoxyamino group where (C₇ -C₁₀) is selected from benzyloxy,2-phenylethoxy, α-phenylethoxy, (2-naphthyl)methoxy,(1-naphthyl)methoxy, or phenylpropoxy; straight or branched (C₁-C₃)alkyl group selected from methyl, ethyl, n-propyl, or 1-methylethyl;(C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl or β-naphthyl;substituted (C₆ -C₁₀)aryl group where the substitution is selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy; a heterocycle groupselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom, optionally having a benzo or pyrido ring fusedthereto, selected from ##STR267## where Z=N, O, S or Se; or a fivemembered aromatic ring with two N, O, S or Se heteroatoms, optionallyhaving a benzo or pyrido ring fused thereto, selected from ##STR268##wherein Z and Z¹ are independently N, O, S or Se; or a five memberedsaturated ring with one or two N, O, S or Se heteroatoms and an adjacentappended O heteroatom selected from ##STR269## wherein A is selectedfrom hydrogen; straight or branched (C₁ -C₄)alkyl; C₆ -aryl; substitutedC₆ -aryl where the substitution is selected from halo, (C₁ -C₄)alkoxy,trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁-C₃)alkylamino or carboxy; (C₇ -C₉)aralkyl group selected from benzyl,1-phenylethyl, 2-phenylethyl or phenylpropyl; or a six membered aromaticring with one to three N heteroatoms, or a six membered saturated ringwith one or two N, O, S, or Se heteroatoms and an adjacent appended Oheteroatom;and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=1-4, R⁴ isselected from hydrogen; amino; straight or branched (C₁ -C₃)alkyl groupselected from methyl, ethyl, n-propyl, or 1-methylethyl; (C₆ -C₁₀)arylgroup selected from phenyl, α-naphthyl or, β-naphthyl; substituted (C₆-C₁₀)aryl group where the substitution is selected from halo, (C₁-C₄)alkyl, nitro, cyano, thiol, amino, carboxy or di-(C₁ -C₃)alkylamino;(C₇ -C₁₀)aralkoxy group; (C₁ -C₄)carboxyalkyl group; or apharmacologically acceptable organic or inorganic salt or metal complexthereof.
 3. A compound according to claim 1 whereinY is selected from--N₂ ⁺ Cl⁻ or N₃ ; X is selected from halogen ortrifluoromethanesulfonyloxy; the halogen is selected from bromine,chlorine, fluorine or iodine; R or R¹ is selected from nitro; amino;halogen selected from chlorine, bromine, fluorine, or iodine; cyano;hydroxy; or --NR² R³ ; R² is selected from hydrogen, methyl, ethyl,n-propyl, 1-methylethyl, n-butyl, and 1-methylpropyl; R³ is selectedfrom methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl, 1,1-dimethylethyl, R⁴ (CH₂)_(n) CO-- or R^(4') (CH₂)_(n)SO₂ --; where n=0-4;with the proviso that when R or R¹ =--NR² R³ and R²=hydrogen, R³ =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, R⁴ (CH₂)_(n) CO-- orR^(4') (CH₂)_(n) SO₂ --;and when R² =methyl or ethyl, R³ =methyl, ethyl,n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl;andwhen R³ is selected from R⁴ (CH₂)_(n) CO-- and n=0, R⁴ is selected fromhydrogen; amino; hydroyamino; straight or branched mono(C₁-C₆)alkylamino group where (C₁ -C₆)alkyl is selected from methyl, ethyl,n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 1-methyl-1-ethylpropyl and the diastereomers andenantiomers of said straight or branched mono(C₁ -C₆)alkylamino group;(C₃ -C₈)cycloalkylamino group where (C₃ -C₈)cycloalkyl is selected fromcyclopropyl, trans-1,2-dimethylcyclopropyl, cis-1,2-dimethylcyclopropyl,trans-2,3-dimethylcyclopropyl, cis-2,3-dimethylcyclopropyl, cyclobutyl,trans-2,3-dimethylcyclobutyl, cis-2,3-dimethylcyclobutyl, cyclopentyl,cyclohexyl, cycloheptyl, cyclooctyl, bicyclo 2.2.1!hept-2-yl, bicyclo2.2.2!oct-2-yl and the diastereomers and enantiomers of said (C₃-C₈)cycloalkylamino group; straight or branched chain di-(C₁-C₆)alkylamino group selected from dimethylamino, diethylamino,methyl(ethyl)amino, ethyl(1-methylethyl)amino or where each (C₁-C₆)alkyl is independently selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 1-methyl-ethylpropyl and the diastereomers andenantiomers of said straight or branched chain di-(C₁ -C₆)alkylaminogroup; (C₁ -C₆)alkoxyamino group where (C₁ -C₆)alkoxy is selected frommethoxy, ethoxy, propoxy, butoxy, pentoxy, or hexoxy; (C₃-C₈)cycloalkoxyamino group where (C₃ -C₈)alkoxy is selected fromcyclopropoxy, trans-1,2-dimethylcyclopropoxy,cis-1,2-dimethylcyclopropoxy, trans-2,3-dimethylcyclopropoxy,cis-2,3-dimethylcyclopropoxy, cyclobutoxy,trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, bicyclo 2.2.1!oct-2-yloxy and the diastereomers andenantiomers of said (C₃ -C₈)cycloalkyloxyamino group; (C₇-C₁₀)aralkoxyamino group where (C₇ -C₁₀) is selected from benzyloxy,2-phenylethoxy, α-phenylethoxy, (2-naphthyl)methoxy,(1-naphthyl)methoxy, or phenylpropoxy; (C₂ -C₈)azacycloalkyl groupselected from aziridinyl, azetidinyl, pyrrolidinyl, pyrrolinyl,piperidinyl, 2-methylpyrrolidinyl, cis-3,4-dimethylpyrrolidinyl,trans-3,4-dimethylpyrrolidinyl, 2-azabicyclo 2.1.1!hex-2-yl,5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo 2.2.1!hept-2-yl, 7-azabicyclo2.2.1!hept-2-yl, 2-azabicyclo 2.2.2!oct-2-yl and the diastereomers andenantiomers of said (C₂ -C₈)azacycloalkyl group; azaheterocycloalkylgroup selected from morpholinyl, piperazinyl, 4-methylpiperazinyl,4-hydroxypiperazinyl, 4-(C₁ -C₄)alkoxy-piperazinyl, thiamorphinyl,tetrahydro-1,2-oxazinyl, isoxazolidinyl, pyrazolidinyl,2-methylpyrazolidinyl, 2,5-diazabicyclo 2.2.2!hept-2-yl,2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl, and diastereomers andenantiomers of said azaheterocycloalkyl group; (C₇ -C₁₀)aralkylaminogroup where (C₇ -C₁₀)aralkyl is selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl, or phenylpropyl;straight or branched (C₁ -C₃)alkyl group selected from methyl, ethyl,n-propyl, or 1-methylethyl; (C₃ -C₆)cycloalkyl group selected fromcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl; substituted (C₃-C₆)cycloalkyl group where the substitution is selected from (C₁-C₃)alkyl, cyano, amino or (C₁ -C₃)acyl; (C₆ -C₁₀)aryl group selectedfrom phenyl, α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl groupwhere the substitution is selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁-C₃)alkyl, nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁-C₃)alkylamino or carboxy; α-hydroxy-(C₁ -C₃)alkyl group selected fromhydroxymethyl, α-hydroxyethyl, α-hydroxy-1-methylethyl, orα-hydroxypropyl; halo(C₁ -C₃)alkyl group; a heterocycle group selectedfrom a five membered aromatic or saturated ring with one N, O, S or Seheteroatom, optionally having a benzo or pyrido ring fused thereto,selected from ##STR270## where Z=N, O, S or Se; or a five memberedaromatic ring with two N, O, S or Se heteroatoms, optionally having abenzo or pyrido ring fused thereto, selected from ##STR271## wherein Zand Z¹ are independently N, O, S or Se; or a five membered saturatedring with one or two N, O, S or Se heteroatoms and an adjacent appendedO heteroatom selected from ##STR272## wherein A is selected fromhydrogen; straight or branched (C₁ -C₄)alkyl; C₆ -aryl; substituted C₆-aryl where the substitution is selected from halo, (C₁ -C₄)alkoxy,trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁-C₃)alkylamino or carboxy; (C₇ -C₉)aralkyl group selected from benzyl,1-phenylethyl, 2-phenylethyl or phenylpropyl; or a six membered aromaticring with one to three N heteroatoms, or a six membered saturated ringwith one or two N, O, S, or Se heteroatoms and an adjacent appended Oheteroatom; acyl or haloacyl group selected from acetyl, propionyl,chloroacetyl, trifluoroacetyl, (C₃ -C₆)cycloalkylcarbonyl, (C₆-C₁₀)aroyl selected from benzoyl or naphthoyl, halo substituted (C₆-C₁₀)aroyl, (C₁ -C₄)alkylbenzoyl, or (heterocycle)carbonyl, theheterocycle selected from a five membered aromatic or saturated ringwith one N, O, S or Se heteroatom, optionally having a benzo or pyridoring fused thereto, selected from ##STR273## where Z=N, O, S or Se; or afive membered aromatic ring with two N, O, S or Se heteroatoms,optionally having a benzo or pyrido ring fused thereto, selected from##STR274## wherein Z and Z¹ are independently N, O, S or Se; or a fivemembered saturated ring with one or two N, O, S or Se heteroatoms and anadjacent appended O heteroatom selected from ##STR275## wherein A isselected from hydrogen; straight or branched (C₁ -C₄)alkyl; C₆ -aryl;substituted C₆ -aryl where the substitution is selected from halo, (C₁-C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy; (C₇ -C₉)aralkyl groupselected from benzyl, 1-phenylethyl, 2-phenylethyl or phenylpropyl; or asix membered aromatic ring with one to three N heteroatoms, or a sixmembered saturated ring with one or two N, O, S, or Se heteroatoms andan adjacent appended O heteroatom; (C₁ -C₄)alkoxycarbonyl group selectedfrom methoxycarbonyl, ethoxycarbonyl, straight or branchedpropoxycarbonyl, straight butoxycarbonyl, or allyloxycarbonyl; vinyl orsubstituted vinyl group where the substitution is selected from (C₁-C₃)alkyl group, halogen, (C₆ -C₁₀)aryl group selected from phenyl,α-naphthyl, β-naphthyl, substituted (C₆ -C₁₀)aryl group where thesubstitution is selected from halo, (C₁ -C₄)alkoxy, trihalo(C₁-C₃)alkyl, nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁-C₃)alkylamino or carboxy; halo(C₁ -C₃)alkyl group, a heterocycle groupselected froma five membered aromatic or saturated ring with one N, O, Sor Se heteroatom, optionally having a benzo or pyrido ring fusedthereto, selected from ##STR276## where Z=N, O, S or Se; (C₁ -C₄)alkoxygroup; C₆ -aryloxy group selected from phenoxy or substituted phenoxywhere the substitution is selected from halo, (C₁ -C₄)alkyl; (C₇-C₁₀)aralkoxy group;and when R³ =R⁴ (CH₂)_(n) CO-- and n=1-4, R⁴ isselected from hydrogen; straight or branched (C₁ -C₄)alkyl groupselected from methyl, ethyl, n-propyl, or 1-methylethyl; (C₆ -C₁₀)arylgroup selected from phenyl, α-naphthyl or, β-naphthyl; substituted (C₆-C₁₀)aryl group where the substitution is selected from halo, (C₁-C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -₃)alkylamino or carboxy; acyloxy or haloacyloxygroup where acyl or haloacyl is selected from acetyl, propionyl,chloroacetyl, trichloroacetyl, (C₃ -C₆)cycloalkylcarbonyl, (C₆-C₁₀)aroyl selected from benzoyl or naphthoyl, halo substituted(C₆-C₁₀)aroyl, (C₁ -C₄)alkylbenzoyl, (heterocycle)carbonyl, the heterocycleselected from a five membered aromatic or saturated ring with one N, O,S or Se heteroatom, optionally having a benzo or pyrido ring fusedthereto, selected from ##STR277## where Z=N, O, S or Se; or a fivemembered aromatic ring with two N, O, S or Se heteroatoms, optionallyhaving a benzo or pyrido ring fused thereto, selected from ##STR278##wherein Z and Z¹ are independently N, O, S or Se; or a five memberedsaturated ring with one or two N, O, S or Se heteroatoms and an adjacentappended O heteroatom selected from ##STR279## wherein A is selectedfrom hydrogen; straight or branched (C₁ -C₄)alkyl; C₆ -aryl;substitutedC₆ -aryl where the substitution is selected from halo, (C₁ -C₄)alkoxy,trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁-C₃)alkylamino or carboxy; (C₇ -C₉)aralkyl group selected from benzyl,1-phenylethyl, 2-phenylethyl or phenylpropyl; or a six membered aromaticring with one to three N heteroatoms, or a six membered saturated ringwith one or two N, O, S, or Se heteroatoms and an adjacent appended Oheteroatom; (C₁ -C₄)alkoxy group; C₆ -aryloxy group selected fromphenoxy or substituted phenoxy where the substitution is selected fromhalo, (C₁ -C₄)alkyl, nitro, cyano, thiol, amino, carboxy, or di-(C₁-C₃)alkylamino; (C₁ -C₃)alkylthio group selected from methylthio,ethylthio, propylthio or allylthio; C₆ -arylthio group selected fromphenylthio or substituted phenylthio where the substitution is selectedfrom halo (C₁ -C₄)alkyl, nitro, cyano, thio, amino, carboxy, di-(C₁-C₃)alkylamino; C₆ -arylsulfonyl group selected from phenylsulfonyl orsubstituted phenylsulfonyl where the substitution is selected from halo,(C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy; a heterocycle groupselected froma five membered aromatic or saturated ring with one N, O, Sor Se heteroatom, optionally having a benzo or pyrido ring fusedthereto, selected from ##STR280## where Z=N, O, S or Se; or a fivemembered aromatic ring with two N, O, S or Se heteroatoms, optionallyhaving a benzo or pyrido ring fused thereto, selected from ##STR281##wherein Z and Z¹ are independently N, O, S or Se; or a five memberedsaturated ring with one or two N, O, S or Se heteroatoms and an adjacentappended O heteroatom selected from ##STR282## wherein A is selectedfrom hydrogen; straight or branched (C₁ -C₄)alkyl; C₆ -aryl; substitutedC₆ -aryl where the substitution is selected from halo, (C₁ -C₄)alkoxy,trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁ -C₄)alkoxycarbonyl, (C₁-C₃)alkylamino or carboxy; (C₇ -C₉)aralkyl group selected from benzyl,1-phenylethyl, 2-phenylethyl or phenylpropyl; or a six membered aromaticring with one to three N heteroatoms, or a six membered saturated ringwith one or two N, O, S, or Se heteroatoms and an adjacent appended Oheteroatom; hydroxy group; α-hydroxy(C₁ -C₃)alkyl group selected fromhydroxymethy, α-hydroxyethyl, α-hydroxy-1-methylethyl orα-hydroxypropyl; halo(C₁ -C₃)alkyl group; acyl or haloacyl groupselected from acetyl, propionyl, chloroacetyl, trifluoroacetyl, (C₃-C₆)cycloalkylcarbonyl, (C₆ -C₁₀)aroyl selected from benzoyl ornaphthoyl, halo substituted (C₆ -C₁₀)aroyl, (C₁ -C₄)alkylbenzoyl, or(heterocycle)carbonyl, the heterocycle selected from a five memberedaromatic or saturated ring with one N, O, S or Se heteroatom, optionallyhaving a benzo or pyrido ring fused thereto, selected from ##STR283##where Z=N, O, S or Se; or a five membered aromatic ring with two N, O, Sor Se heteroatoms, optionally having a benzo or pyrido ring fusedthereto, selected from ##STR284## wherein Z and Z¹ are independently N,O, S or Se; or a five membered saturated ring with one or two N, O, S orSe heteroatoms and an adjacent appended O heteroatom selected from##STR285## wherein A is selected from hydrogen; straight or branched (C₁-C₄)alkyl; C₆ -aryl; substituted C₆ -aryl where the substitution isselected from halo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino,cyano, (C₁ -C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy; (C₇-C₉)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl orphenylpropyl; or a six membered aromatic ring with one to three Nheteroatoms, or a six membered saturated ring with one or two N, O, S,or Se heteroatoms and an adjacent appended O heteroatom;and when R³ =R⁴(CH₂)_(n) CO-- and n=2-4, R⁴ is additionally selected from amino;hydroyamino; straight or branched mono(C₁ -C₆)alkylamino group where (C₁-C₆)alkyl is selected from methyl, ethyl, n-propyl, 1-methylethyl,n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,1-methyl-1-ethylpropyl and the diastereomers and enantiomers of saidstraight or branched mono(C₁ -C₆)alkylamino group; (C₃-C₈)cycloalkylamino group where (C₃ -C₈)cycloalkyl is selected fromcyclopropyl, trans-1,2-dimethylcyclopropyl, cis-1,2-dimethylcyclopropyl,trans-2,3-dimethylcyclopropyl, cis-2,3-dimethylcyclopropyl, cyclobutyl,trans-2,3-dimethylcyclobutyl, cis-2,3-dimethylcyclobutyl, cyclopentyl,cyclohexyl, cycloheptyl, cyclooctyl, bicyclo 2.2.1!hept-2-yl, bicyclo2.2.2!oct-2-yl and the diastereomers and enantiomers of said (C₃-C₈)cycloalkylamino group; straight or branched chain di-(C₁-C₆)alkylamino group selected from dimethylamino, diethylamino,methyl(ethyl)amino, ethyl(1-methylethyl)amino or where each (C₁-C₆)alkyl is independently selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 1-methyl-ethylpropyl and the diastereomers andenantiomers of said straight or branched chain di-(C₁ -C₆)alkylaminogroup; (C₁ -C₆)alkoxyamino group where (C₁ -C₆)alkoxy is selected frommethoxy, ethoxy, propoxy, butoxy, pentoxy, or hexoxy; (C₃-C₈)cycloalkoxyamino group where (C₃ -C₈)alkoxy is selected fromcyclopropoxy, trans-1,2-dimethylcyclopropoxy,cis-1,2-dimethylcyclopropoxy, trans-2,3-dimethylcyclopropoxy,cis-2,3-dimethylcyclopropoxy, cyclobutoxy,trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, bicyclo 2.2.1!oct-2-yloxy and the diastereomers andenantiomers of said (C₃ -C₈)cycloalkyloxyamino group; (C₇-C₁₀)aralkoxyamino group where (C₇ -C₁₀) is selected from benzyloxy,2-phenylethoxy, α-phenylethoxy, (2-naphthyl)methoxy,(1-naphthyl)methoxy, or phenylpropoxy; (C₂ -C₈)azacycloalkyl groupselected from aziridinyl, azetidinyl, pyrrolidinyl, pyrrolinyl,piperidinyl, 2-methylpyrrolidinyl, cis-3,4-dimethylpyrrolidinyl,trans-3,4-dimethylpyrrolidinyl, 2-azabicyclo 2.1.1!hex-2-yl,5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo 2.2.1!hept-2-yl, 7-azabicyclo2.2.1!hept-2-yl, 2-azabicyclo 2.2.2!oct-2-yl and the diastereomers andenantiomers of said (C₂ -C₈)azacycloalkyl group; azaheterocycloalkylgroup selected from morpholinyl, piperazinyl, 4-methylpiperazinyl,4-hydroxypiperazinyl, 4-(C₁ -C₄)alkoxy-piperazinyl, thiamorphinyl,tetrahydro-1, 2-oxazinyl, isoxazolidinyl, pyrazolidinyl,2-methylpyrazolidinyl, 2,5-diazabicyclo 2.2.2!hept-2-yl,2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl, and diastereomers andenantiomers of said azaheterocycloalkyl group; (C₇ -C₁₀)aralkylaminogroup where (C₇ -C₁₀)aralkyl is selected from benzyl, 2-phenylethyl,α-phenylethyl, (2-naphthyl)methyl, (1-naphthyl)methyl, or phenylpropyl;(C₁ -C₄)alkoxycarbonylamino group selected from n-butoxycarbonylamino,allyloxycarbonylamino, methoxycarbonylamino, ethoxycarbonylamino, orpropoxycarbonylamino;and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=0,R^(4') is selected from amino; hydroyamino; straight or branched mono(C₁-C₆)alkylamino group where (C₁ -C₆)alkyl is selected from methyl, ethyl,n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 1-methyl-1-ethylpropyl and the diastereomers andenantiomers of said straight or branched mono(C₁ -C₆)alkylamino group;(C₃ -C₈)cycloalkylamino group where (C₃ -C₈) cycloalkyl is selected fromcyclopropyl, trans-1,2-dimethylcyclopropyl, cis-1,2-dimethylcyclopropyl,trans-2,3-dimethylcyclopropyl, cis-2,3-dimethylcyclopropyl, cyclobutyl,trans-2,3-dimethylcyclobutyl, cis-2,3-dimethylcyclobutyl, cyclopentyl,cyclohexyl, cycloheptyl, cyclooctyl, bicyclo 2.2.1!hept-2-yl, bicyclo2.2.2!oct-2-yl and the diastereomers and enantiomers of said (C₃-C₈)cycloalkylamino group; straight or branched chain di-(C₁-C₆)alkylamino group selected from dimethylamino, diethylamino,methyl(ethyl)amino, ethyl(1-methylethyl)amino or where each (C₁-C₆)alkyl is independently selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 1-methyl-ethylpropyl and the diastereomers andenantiomers of said straight or branched chain di-(C₁ -C₆)alkylaminogroup; (C₁ -C₆)alkoxyamino group where (C₁ -C₆)alkoxy is selected frommethoxy, ethoxy, propoxy, butoxy, pentoxy, or hexoxy; (C₃-C₈)cycloalkoxyamino group where (C₃ -C₈)alkoxy is selected fromcyclopropoxy, trans-1,2-dimethylcyclopropoxy,cis-1,2-dimethylcyclopropoxy, trans-2,3-dimethylcyclopropoxy,cis-2,3-dimethylcyclopropoxy, cyclobutoxy,trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, bicyclo 2.2.1!oct-2-yloxy and the diastereomers andenantiomers of said (C₃ -C₈)cycloalkyloxyamino group; (C₇-C₁₀)aralkoxyamino group where (C₇ -C₁₀) is selected from benzyloxy,2-phenylethoxy, α-phenylethoxy, (2-naphthyl)methoxy,(1-naphthyl)methoxy, or phenylpropoxy; straight or branched (C₁-C₃)alkyl group selected from methyl, ethyl, n-propyl, or 1-methylethyl;(C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl or β-naphthyl;substituted (C₆ -C₁₀)aryl group where the substitution is selected fromhalo, (C₁ -C₄)alkoxy, trihalo(C₁ -C₃)alkyl, nitro, amino, cyano, (C₁-C₄)alkoxycarbonyl, (C₁ -C₃)alkylamino or carboxy; a heterocycle groupselected froma five membered aromatic or saturated ring with one N, O, Sor Se heteroatom, optionally having a benzo or pyrido ring fusedthereto, selected from ##STR286## where Z=N, O, S or Se; and when R³=R^(4') (CH₂)_(n) SO₂ -- and n=1-4, R^(4') is selected from hydrogen;amino; straight or branched (C₁ -C₃)alkyl group selected from methyl,ethyl, n-propyl, or 1-methylethyl; or a pharmacologically acceptableorganic or inorganic salt or metal complex thereof.
 4. A compoundaccording to claim 1 whereinY is selected from --N₂ ⁺ Cl⁻ or N₃ ; X isselected from halogen or trifluoromethanesulfonyloxy; the halogen isselected from bromine, chlorine, fluorine or iodine; R or R¹ is selectedfrom nitro; amino; halogen selected from chlorine, bromine, fluorine, oriodine; cyano; hydroxy; or --NR² R³ ; R² is selected from hydrogen,methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, and 1-methylpropyl; R³is selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, R⁴ (CH₂)_(n) CO-- orR^(4') (CH₂)_(n) SO₂ --; where n=0-4;with the proviso that when R or R¹=--NR² R³ and R² =hydrogen, R³ =methyl, ethyl, n-propyl, 1-methylethyl,n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, R⁴ (CH₂)_(n)CO-- or R^(4') (CH₂)_(n) SO₂ --;and when R² =methyl or ethyl, R³=methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or2-methylpropyl;and when R³ is selected from R⁴ (CH₂)_(n) CO-- and n=0,R⁴ is selected from hydrogen; amino; hydroyamino; straight or branchedmono(C₁ -C₆)alkylamino group where (C₁ -C₆)alkyl is selected frommethyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 2-methylbutyl,1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl, n-hexyl,1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl,1,2-dimethylbutyl, 1,3-dimethylbutyl, 1-methyl-1-ethylpropyl and thediastereomers and enantiomers of said straight or branched mono(C₁-C₆)alkylamino group; (C₃ -C₈)cycloalkylamino group where (C₃-C₈)cycloalkyl is selected from cyclopropyl,trans-1,2-dimethylcyclopropyl, cis-1,2-dimethylcyclopropyl,trans-2,3-dimethylcyclopropyl, cis-2,3-dimethylcyclopropyl, cyclobutyl,trans-2,3-dimethylcyclobutyl, cis-2,3-dimethylcyclobutyl, cyclopentyl,cyclohexyl, cycloheptyl, cyclooctyl, bicyclo 2.2.1!hept-2-yl, bicyclo2.2.2!oct-2-yl and the diastereomers and enantiomers of said (C₃-C₈)cycloalkylamino group; straight or branched chain di-(C₁C₆)alkylamino group selected from dimethylamino, diethylamino,methyl(ethyl)amino, ethyl(1-methylethyl)amino or where each (C₁-C₆)alkyl is independently selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 1-methyl-ethylpropyl and the diastereomers andenantiomers of said straight or branched chain di-(C₁ -C₆)alkylaminogroup; (C₁ -C₆)alkoxyamino group where (C₁ -C₆)alkoxy is selected frommethoxy, ethoxy, propoxy, butoxy, pentoxy, or hexoxy; (C₃-C₈)cycloalkoxyamino group where (C₃ -C₈)alkoxy is selected fromcyclopropoxy, trans-1,2-dimethylcyclopropoxy,cis-1,2-dimethylcyclopropoxy, trans-2,3-dimethylcyclopropoxy,cis-2,3-dimethylcyclopropoxy, cyclobutoxy,trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, bicyclo 2.2.1!oct-2-yloxy and the diastereomers andenantiomers of said (C₃₋ C₈)cycloalkyloxyamino group; (C₇-C₁₀)aralkoxyamino group where (C₇ -C₁₀) is selected from benzyloxy,2-phenylethoxy, α-phenylethoxy, (2-naphthyl)methoxy,(1-naphthyl)methoxy, or phenylpropoxy; (C₂ -C₈)azacycloalkyl groupselected from aziridinyl, azetidinyl, pyrrolidinyl, pyrrolinyl,piperidinyl, 2-methylpyrrolidinyl, cis-3,4-dimethylpyrrolidinyl,trans-3,4-dimethylpyrrolidinyl, 2-azabicyclo 2.1.1!hex-2-yl,5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo 2.2.1!hept-2-yl, 7-azabicyclo2.2.1!hept-2-yl, 2-azabicyclo 2.2.2!oct-2-yl and the diastereomers andenantiomers of said (C₂ -C₈)azacycloalkyl group; azaheterocycloalkylgroup selected from morpholinyl, piperazinyl, 4-methylpiperazinyl,4-hydroxypiperazinyl, 4-(C₁ -C₄)alkoxy-piperazinyl, thiamorphinyl,tetrahydro-1,2-oxazinyl, isoxazolidinyl, pyrazolidinyl,2-methylpyrazolidinyl, 2,5-diazabicyclo 2.2.2!hept-2-yl,2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl, and diastereomers andenantiomers of said azaheterocycloalkyl group; straight or branched (C₁-C₂)alkyl group selected from methyl or ethyl; (C₆ -C₁₀)aryl groupselected from phenyl, α-naphthyl or β-naphthyl; substituted (C₆-C₁₀)aryl group where the substitution is selected from halo, (C₁-C₄)alkoxy, nitro, or amino; hydroxymethyl; halo (C₁ -C₃)alkyl group; aheterocycle group selected from a five membered aromatic or saturatedring with one N, O, S or Se heteroatom, optionally having a benzo orpyrido ring fused thereto, selected from ##STR287## where Z=N, O, S orSe; or a five membered aromatic ring with two N, O, S or Se heteroatoms,optionally having a benzo or pyrido ring fused thereto, selected from##STR288## wherein Z and Z¹ are independently N, O, S or Se; (C₁-C₄)alkoxycarbonyl group selected from methoxycarbonyl, ethoxycarbonyl,straight or branched propoxycarbonyl, straight butoxycarbonyl, orallyloxycarbonyl; vinyl or substituted vinyl group where thesubstitution is selected from (C₁ -C₃)alkyl group, (C₆ -C₁₀)aryl groupselected from phenyl, α-naphthyl, β-naphthyl, and when R³ =R⁴ (CH₂)_(n)CO-- and n=1-4, R⁴ is selected from hydrogen; (C₁ -C₂)alkyl groupselected from methyl or ethyl; (C₆ -C₁₀)aryl group selected from phenyl,α-naphthyl or β-naphthyl; substituted (C₆ -C₁₀)aryl group where thesubstitution is selected from halo, (C₁ -C₄)alkoxy or trihalo(C₁-C₃)alkyl; acyloxy or haloacyloxy group where acyl or haloacyl isselected from acetyl, propionyl, chloroacetyl, trichloroacetyl, (C₃-C₆)cycloalkylcarbonyl, (C₆ -C₁₀)aroyl selected from benzoyl ornaphthoyl, halo substituted(C₆ -C₁₀)aroyl, (C₁ -C₄)alkylbenzoyl,(heterocycle)carbonyl, the heterocycle selected froma five memberedaromatic or saturated ring with one N, O, S or Se heteroatom, optionallyhaving a benzo or pyrido ring fused thereto, selected from ##STR289##where Z=N, O, S or Se; or a five membered aromatic ring with two N, O, Sor Se heteroatoms, optionally having a benzo or pyrido ring fusedthereto, selected from ##STR290## wherein Z and Z¹ are independently N,O, S or Se; or a six membered aromatic ring with one or two Nheteroatoms; (C₁ -C₄)alkoxy group; α-hydroxy(C₁ -C₃)alkyl group selectedfrom hydroxymethy, α-hydroxyethyl, α-hydroxy-1-methylethyl orα-hydroxypropyl; halo(C₁ -C₃)alkyl group;and when R³ =R⁴ (CH₂)_(n) CO--and n=2-4, R⁴ is additionally selected from amino; hydroyamino; straightor branched mono(C₁ -C₆)alkylamino group where (C₁ -C₆)alkyl is selectedfrom methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 2-methylbutyl,1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl, n-hexyl,1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl,1,2-dimethylbutyl, 1,3-dimethylbutyl, 1-methyl-1-ethylpropyl and thediastereomers and enantiomers of said straight or branched mono(C₁-C₆)alkylamino group; (C₃ -C₈)cycloalkylamino group where (C₃-C₈)cycloalkyl is selected from cyclopropyl,trans-1,2-dimethylcyclopropyl, cis-1,2-dimethylcyclopropyl,trans-2,3-dimethylcyclopropyl, cis-2,3-dimethylcyclopropyl, cyclobutyl,trans-2,3-dimethylcyclobutyl, cis-2,3-dimethylcyclobutyl, cyclopentyl,cyclohexyl, cycloheptyl, cyclooctyl, bicyclo 2.2.1!hept-2-yl, bicyclo2.2.2!oct-2-yl and the diastereomers and enantiomers of said (C₃-C₈)cycloalkylamino group; straight or branched chain di-(C₁-C₆)alkylamino group selected from dimethylamino, diethylamino,methyl(ethyl)amino, ethyl(1-methylethyl)amino or where each (C₁-C₆)alkyl is independently selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 1-methyl-ethylpropyl and the diastereomers andenantiomers of said straight or branched chain di-(C₁ -C₆)alkylaminogroup; (C₁ -C₆)alkoxyamino group where (C₁ -C₆)alkoxy is selected frommethoxy, ethoxy, propoxy, butoxy, pentoxy, or hexoxy; (C₃-C₈)cycloalkoxyamino group where (C₃ -C₈)alkoxy is selected fromcyclopropoxy, trans-1,2-dimethylcyclopropoxy,cis-1,2-dimethylcyclopropoxy, trans-2,3-dimethylcyclopropoxy,cis-2,3-dimethylcyclopropoxy, cyclobutoxy,trans-2,3-dimethylcyclobutoxy, cis-2,3-dimethylcyclobutoxy,cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, bicyclo2.2.1!hept-2-yloxy, bicyclo 2.2.1!oct-2-yloxy and the diastereomers andenantiomers of said (C₃ -C₈)cycloalkyloxyamino group; (C₇-C₁₀)aralkoxyamino group where (C₇ -C₁₀) is selected from benzyloxy,2-phenylethoxy, α-phenylethoxy, (2-naphthyl)methoxy,(1-naphthyl)methoxy, or phenylpropoxy; (C₂ -C₈)azacycloalkyl groupselected from aziridinyl, azetidinyl, pyrrolidinyl, pyrrolinyl,piperidinyl, 2-methylpyrrolidinyl, cis-3,4-dimethylpyrrolidinyl,trans-3,4-dimethylpyrrolidinyl, 2-azabicyclo 2.1.1!hex-2-yl,5-azabicyclo 2.1.1!hex-5-yl, 2-azabicyclo 2.2.1!hept-2-yl, 7-azabicyclo2.2.1!hept-2-yl, 2-azabicyclo 2.2.2!oct-2-yl and the diastereomers andenantiomers of said (C₂ -C₈)azacycloalkyl group; azaheterocycloalkylgroup selected from morpholinyl, piperazinyl, 4-methylpiperazinyl,4-hydroxypiperazinyl, 4-(C₁ -C₄)alkoxy-piperazinyl, thiamorphinyl,tetrahydro-1,2-oxazinyl, isoxazolidinyl, pyrazolidinyl,2-methylpyrazolidinyl, 2,5-diazabicyclo 2.2.2!hept-2-yl,2,5-diaza-5-methylbicyclo 2.2.1!hept-2-yl, and diastereomers andenantiomers of said azaheterocycloalkyl group; (C₁-C₄)alkoxycarbonylamino group selected from n-butoxycarbonylamino,allyloxycarbonylamino, methoxycarbonylamino, ethoxycarbonylamino, orpropoxycarbonylamino;and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=0,R^(4') is selected from amino; hydroyamino; straight or branched mono(C₁-C₆)alkylamino group where (C₁ -C₆)alkyl is selected from methyl, ethyl,n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 2-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 1-methyl-1-ethylpropyl and the diastereomers andenantiomers of said straight or branched mono(C₁ -C₆)alkylamino group;straight or branched chain di-(C₁ -C₆)alkylamino group selected fromdimethylamino, diethylamino, methyl(ethyl)amino,ethyl(1-methylethyl)amino or where each (C₁ -C₆)alkyl is independentlyselected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl,n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,1-methyl-ethylpropyl and the diastereomers and enantiomers of saidstraight or branched chain di-(C₁ -C₆)alkylamino group; straight orbranched (C₁ -C₂)alkyl group selected from methyl or ethyl; (C₆-C₁₀)aryl group selected from phenyl, α-naphthyl or, β-naphthyl;and whenR³ =R^(4') (CH₂)_(n) SO₂ -- and n=1-4, R⁴ is selected from hydrogen;straight or branched (C₁ -C₂)alkyl group selected from methyl or ethyl;or a pharmacologically acceptable organic or inorganic salt or metalcomplex thereof.
 5. A compound of claim 1 whereinY is selected from --N₂⁺ Cl⁻ or N₃ ; X is selected from halogen or trifluoromethanesulfonyloxy;the halogen is selected from bromine, chlorine, fluorine or iodine; R orR¹ is selected from nitro; amino; halogen selected from chlorine,bromine, fluorine, or iodine; cyano; hydroxy; or --NR² R³ ; R² isselected from hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,and 1-methylpropyl; R³ is selected from methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, R⁴ (CH₂)_(n) CO-- or R^(4') (CH₂)_(n) SO₂ --; wheren=0-4;with the proviso that when R or R¹ =--NR² R³ and R² =hydrogen, R³=methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl,2-methylpropyl, 1,1-dimethylethyl, R⁴ (CH₂)_(n) CO-- or R^(4') (CH₂)_(n)SO₂ --;and when R² =methyl or ethyl, R³ =methyl or ethyl;and when R³ isselected from R⁴ (CH₂)_(n) CO-- and n=0, R⁴ is selected from hydrogen;straight or branched (C₁ -C₂)alkyl group selected from methyl or ethyl;a heterocycle group selected from a five membered aromatic or saturatedring with one N, O, S or Se heteroatom, optionally having a benzo orpyrido ring fused thereto, selected from ##STR291## where Z=N, O, S orSe; or a five membered aromatic ring with two N, O, S or Se heteroatoms,optionally having a benzo or pyrido ring fused thereto, selected from##STR292## wherein Z and Z¹ are independently N, O, S or Se; (C₁-C₄)alkoxy group; C₆ -aryloxy group selected from phenoxy or substitutedphenoxy where the substitution is selected from halo or (C₁ -C₄)alkyl;(C₇ -C₁₀)aralkoxy group;and when R³ =R⁴ (CH₂)_(n) CO-- and n=1-4, R⁴ isselected from hydrogen; (C₁ C₂)alkyl group selected from methyl orethyl; (C₆ -C₁₀)aryl group selected from phenyl, α-naphthyl or,β-naphthyl;and when R³ =R^(4') (CH₂)_(n) SO₂ -- and n=0, R^(4') isselected from straight or branched (C₁ -C₃)alkyl group selected frommethyl or ethyl; (C₆ -C₁₀)aryl group selected from phenyl, α-naphthylor, β-naphthyl; or a pharmacologically acceptable organic or inorganicsalt or metal complex thereof.
 6. The compound according to claim 1wherein said inorganic salt comprises aluminum, calcium, iron,magnesium, manganese, and complex salts.
 7. The compound according toclaim 1 wherein said organic salt comprises acetate, benzoate, citrate,cysteine or other amino acids, fumarate glycolate, maleate, succinate,tartrate, alkylsulfonate or arylsulfonate.
 8. The compound according toclaim 1 wherein said metal complex comprises aluminum, calcium, iron,magnesium, manganese, and complex salts.